CN111566097A - 噁二唑化合物或其盐类及含有该化合物的农园艺用杀菌剂、以及其使用方法 - Google Patents
噁二唑化合物或其盐类及含有该化合物的农园艺用杀菌剂、以及其使用方法 Download PDFInfo
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- CN111566097A CN111566097A CN201880083839.2A CN201880083839A CN111566097A CN 111566097 A CN111566097 A CN 111566097A CN 201880083839 A CN201880083839 A CN 201880083839A CN 111566097 A CN111566097 A CN 111566097A
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- cycloalkyl
- alkoxy
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- FROBCXTULYFHEJ-OAHLLOKOSA-N propaquizafop Chemical compound C1=CC(O[C@H](C)C(=O)OCCON=C(C)C)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 FROBCXTULYFHEJ-OAHLLOKOSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 231100000654 protein toxin Toxicity 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 description 1
- AEHJMNVBLRLZKK-UHFFFAOYSA-N pyridalyl Chemical group N1=CC(C(F)(F)F)=CC=C1OCCCOC1=C(Cl)C=C(OCC=C(Cl)Cl)C=C1Cl AEHJMNVBLRLZKK-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- USSIUIGPBLPCDF-KEBDBYFISA-N pyriminobac-methyl Chemical group CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC USSIUIGPBLPCDF-KEBDBYFISA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 244000022778 quail grass Species 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
- FBUIFWSLGSCVCG-UHFFFAOYSA-N quinolin-2-yl prop-2-enoate Chemical compound C1=CC=CC2=NC(OC(=O)C=C)=CC=C21 FBUIFWSLGSCVCG-UHFFFAOYSA-N 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- WRPIRSINYZBGPK-UHFFFAOYSA-N quinoxyfen Chemical compound C1=CC(F)=CC=C1OC1=CC=NC2=CC(Cl)=CC(Cl)=C12 WRPIRSINYZBGPK-UHFFFAOYSA-N 0.000 description 1
- RDYMFSUJUZBWLH-AZVNHNRSSA-N qy5y9r7g0e Chemical compound C([C@H]12)OS(=O)OC[C@@H]1[C@]1(Cl)C(Cl)=C(Cl)[C@@]2(Cl)C1(Cl)Cl RDYMFSUJUZBWLH-AZVNHNRSSA-N 0.000 description 1
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- 238000005215 recombination Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
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- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003001 serine protease inhibitor Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
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- 235000019832 sodium triphosphate Nutrition 0.000 description 1
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- 235000013599 spices Nutrition 0.000 description 1
- 239000002708 spider venom Substances 0.000 description 1
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- 238000004659 sterilization and disinfection Methods 0.000 description 1
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- 229960005322 streptomycin Drugs 0.000 description 1
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- FZMKKCQHDROFNI-UHFFFAOYSA-N sulfometuron Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 FZMKKCQHDROFNI-UHFFFAOYSA-N 0.000 description 1
- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 239000004548 suspo-emulsion Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- LWLJEQHTPVPKSJ-UHFFFAOYSA-N tebufloquin Chemical compound C1=C(C(C)(C)C)C=C2C(OC(=O)C)=C(C)C(C)=NC2=C1F LWLJEQHTPVPKSJ-UHFFFAOYSA-N 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005922 tert-pentoxy group Chemical group 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- LOQQVLXUKHKNIA-UHFFFAOYSA-N thifensulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-UHFFFAOYSA-N 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
- MBNMHBAJUNHZRE-UHFFFAOYSA-M thiosultap monosodium Chemical compound [Na+].OS(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O MBNMHBAJUNHZRE-UHFFFAOYSA-M 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 239000001585 thymus vulgaris Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- XMLSXPIVAXONDL-UHFFFAOYSA-N trans-jasmone Natural products CCC=CCC1=C(C)CCC1=O XMLSXPIVAXONDL-UHFFFAOYSA-N 0.000 description 1
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- RVKCCVTVZORVGD-UHFFFAOYSA-N trinexapac-ethyl Chemical group O=C1CC(C(=O)OCC)CC(=O)C1=C(O)C1CC1 RVKCCVTVZORVGD-UHFFFAOYSA-N 0.000 description 1
- 239000000015 trinitrotoluene Substances 0.000 description 1
- PIHCREFCPDWIPY-UHFFFAOYSA-N tris[2-(2,4-dichlorophenoxy)ethyl] phosphite Chemical compound ClC1=CC(Cl)=CC=C1OCCOP(OCCOC=1C(=CC(Cl)=CC=1)Cl)OCCOC1=CC=C(Cl)C=C1Cl PIHCREFCPDWIPY-UHFFFAOYSA-N 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 229940072651 tylenol Drugs 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- YNWVFADWVLCOPU-MAUPQMMJSA-N uniconazole P Chemical compound C1=NC=NN1/C([C@@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MAUPQMMJSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
在农业及园艺等作物的生产中,病害造成的损害依然很大,由于产生了对现有药物具有耐药性的病害等原因,期待开发一种新型的农园艺用杀菌剂。本发明提供一种以通式(I)表示的化合物或其盐类为有效成分的农园艺用杀菌剂、以及其的使用方法。式中,R1表示(a2)(C1‑C6)烷基等。R2表示(b1)氢原子等。R3表示(c1)氢原子或(c2)(C1‑C6)烷基等。R4表示(d2)(C1‑C6)烷基等。X1、X2、X3及X4表示(e1)氢原子等。Y表示氧原子等。【化学式1】
Description
技术领域
本发明涉及含有噁二唑化合物或其盐类作为有效成分的农园艺用杀菌剂、及其使用方法。
背景技术
专利文献1、2及3中记载了某些种类的噁二唑衍生物对植物病害的致病菌具有杀菌活性。
【现有技术文献】
【专利文献】
【专利文献1】日本特开昭63-162680号公报
【专利文献2】国际公开第2015/185485号小册子
【专利文献3】国际公开第2017/055473号小册子
发明内容
发明要解决的课题
农业和园艺等的作物生产中,病害造成的损害依然很大,由于产生了对现有药物具有耐药性的病害等原因,期待开发新型的农园艺用杀菌剂。
为了解决课题的手段
本发明人等为了开发新的杀菌剂进行了反复深入研究,结果发现,化合物的结构中含有半缩醛胺(ヘミアミナール)结构的特定化合物或其盐类作为农园艺用杀菌剂是有用的,而这一点在上述任何一个公知文献中都没有记载和暗示,从而完成了本发明。
即,本发明涉及下述各项:
[1]通式(I)表示的化合物或其盐类,
【化学式1】
式中,
R1表示:
(a1)氢原子;
(a2)(C1-C6)烷基;
(a3)(C2-C6)烯基;
(a4)(C2-C6)炔基;
(a5)(C3-C6)环烷基;
(a6)卤代(C1-C6)烷基;
(a7)卤代(C2-C6)烯基;
(a8)卤代(C2-C6)炔基;或
(a9)卤代(C3-C6)环烷基,
R2表示:
(b1)氢原子;
(b2)(C1-C6)烷基;
(b3)(C2-C6)烯基;
(b4)(C2-C6)炔基;
(b5)(C3-C6)环烷基;
(b6)卤代(C1-C6)烷基;
(b7)卤代(C2-C6)烯基;
(b8)卤代(C2-C6)炔基;或
(b9)卤代(C3-C6)环烷基,
R3表示:
(c1)氢原子;
(c2)(C1-C6)烷基;
(c3)(C2-C6)烯基;
(c4)(C2-C6)炔基;
(c5)(C3-C6)环烷基;
(c6)(C1-C6)烷基羰基;或
(c7)(C1-C6)烷氧基羰基,
R4表示:
(d1)氢原子;
(d2)(C1-C6)烷基;
(d3)(C2-C6)烯基;
(d4)(C2-C6)炔基;
(d5)(C3-C6)环烷基;
(d6)(C1-C6)烷氧基;
(d7)卤代(C1-C6)烷基;
(d8)卤代(C2-C6)烯基;
(d9)卤代(C2-C6)炔基;
(d10)卤代(C3-C6)环烷基;
(d11)卤代(C1-C6)烷氧基;
(d12)Ra(Rb)N基(式中,Ra及Rb分别独立地表示氢原子、(C1-C6)烷基、(C3-C6)环烷基、(C3-C6)环烷基(C1-C6)烷基、苯基、(C1-C6)烷基羰基或苯基羰基。);
(d13)芳基;
(d14)环上具有1~8个取代基的芳基,所述取代基分别独立地选自由卤素原子、氰基、硝基、(C1-C6)烷基、(C1-C6)烷氧基、(C3-C6)环烷基、卤代(C1-C6)烷基、卤代(C1-C6)烷氧基、卤代(C3-C6)环烷基、(C1-C6)烷基硫基、(C1-C6)烷基亚磺酰基、(C1-C6)烷基磺酰基、卤代(C1-C6)烷基硫基、卤代(C1-C6)烷基亚磺酰基及卤代(C1-C6)烷基磺酰基构成的组;
(d15)杂芳基;
(d16)环上具有1~3个取代基的杂芳基,所述取代基分别独立地选自由卤素原子、氰基、硝基、(C1-C6)烷基、(C1-C6)烷氧基、(C3-C6)环烷基、卤代(C1-C6)烷基、卤代(C1-C6)烷氧基、卤代(C3-C6)环烷基、(C1-C6)烷基硫基、(C1-C6)烷基亚磺酰基、(C1-C6)烷基磺酰基、卤代(C1-C6)烷基硫基、卤代(C1-C6)烷基亚磺酰基及卤代(C1-C6)烷基磺酰基构成的组;
(d17)芳基(C1-C6)烷基;
(d18)环上具有1~8个取代基的芳基(C1-C6)烷基,所述取代基分别独立地选自由卤素原子、氰基、硝基、(C1-C6)烷基、(C1-C6)烷氧基、(C3-C6)环烷基、卤代(C1-C6)烷基、卤代(C1-C6)烷氧基、卤代(C3-C6)环烷基、(C1-C6)烷基硫基、(C1-C6)烷基亚磺酰基、(C1-C6)烷基磺酰基、卤代(C1-C6)烷基硫基、卤代(C1-C6)烷基亚磺酰基及卤代(C1-C6)烷基磺酰基构成的组;
(d19)杂芳基(C1-C6)烷基;
(d20)环上具有1~3个取代基的杂芳基(C1-C6)烷基,所述取代基分别独立地选自由卤素原子、氰基、硝基、(C1-C6)烷基、(C1-C6)烷氧基、(C3-C6)环烷基、卤代(C1-C6)烷基、卤代(C1-C6)烷氧基、卤代(C3-C6)环烷基、(C1-C6)烷基硫基、(C1-C6)烷基亚磺酰基、(C1-C6)烷基磺酰基、卤代(C1-C6)烷基硫基、卤代(C1-C6)烷基亚磺酰基及卤代(C1-C6)烷基磺酰基构成的组;
(d21)链上具有1~3个取代基的(C1-C6)烷基,所述取代基分别独立地选自由氰基、(C1-C6)烷氧基、Ra(Rb)N基(式中,Ra及Rb如上所述。)、(C1-C6)烷基硫基、(C1-C6)烷基亚磺酰基及(C1-C6)烷基磺酰基构成的组;或
(d22)环上具有1~2个氧原子的3元~6元非芳香族杂环基,
X1、X2、X3及X4分别独立地表示:
(e1)氢原子;
(e2)卤素原子;
(e3)氰基;
(e4)硝基;
(e5)(C1-C6)烷基;
(e6)(C3-C6)环烷基;
(e7)(C1-C6)烷氧基;
(e8)卤代(C1-C6)烷基;
(e9)卤代(C1-C6)烷氧基;
(e10)卤代(C3-C6)环烷基;
(e11)(C1-C6)烷基硫基;
(e12)(C1-C6)烷基亚磺酰基;
(e13)(C1-C6)烷基磺酰基;
(e14)卤代(C1-C6)烷基硫基;
(e15)卤代(C1-C6)烷基亚磺酰基;或
(e16)卤代(C1-C6)烷基磺酰基,
Y表示氧原子;或硫原子。
[2]根据[1]所述的化合物或其盐类,其中,
R1为:
(a2)(C1-C6)烷基,
R2为:
(b1)氢原子,
R3为:
(c1)氢原子;
(c2)(C1-C6)烷基;或
(c5)(C3-C6)环烷基,
R4为:
(d2)(C1-C6)烷基;
(d3)(C2-C6)烯基;
(d4)(C2-C6)炔基;
(d5)(C3-C6)环烷基;
(d6)(C1-C6)烷氧基;
(d7)卤代(C1-C6)烷基;
(d12)Ra(Rb)N基(式中,Ra及Rb分别独立地表示、氢原子、(C1-C6)烷基、(C3-C6)环烷基、(C3-C6)环烷基(C1-C6)烷基、苯基、(C1-C6)烷基羰基或苯基羰基。);
(d13)芳基;
(d14)环上具有1~8个取代基的芳基,所述取代基分别独立地选自由卤素原子、氰基、硝基、(C1-C6)烷基、(C1-C6)烷氧基、(C3-C6)环烷基、卤代(C1-C6)烷基、卤代(C1-C6)烷氧基、卤代(C3-C6)环烷基、(C1-C6)烷基硫基、(C1-C6)烷基亚磺酰基、(C1-C6)烷基磺酰基、卤代(C1-C6)烷基硫基、卤代(C1-C6)烷基亚磺酰基及卤代(C1-C6)烷基磺酰基构成的组;
(d15)杂芳基;
(d17)芳基(C1-C6)烷基;
(d21)链上具有1~3个取代基的(C1-C6)烷基,所述取代基分别独立地选自由氰基、(C1-C6)烷氧基、Ra(Rb)N基(式中,Ra及Rb如上所述。)、(C1-C6)烷基硫基、(C1-C6)烷基亚磺酰基及(C1-C6)烷基磺酰基构成的组;或
(d22)环状具有1~2个氧原子的3元~6元非芳香族杂环基,
X1、X2、X3及X4分别独立地为:
(e1)氢原子;
(e2)卤素原子;
(e5)(C1-C6)烷基;
(e7)(C1-C6)烷氧基;
(e11)(C1-C6)烷基硫基;
(e12)(C1-C6)烷基亚磺酰基;或
(e13)(C1-C6)烷基磺酰基,
Y为氧原子;或硫原子。
[3]根据[1]或[2]所述的化合物或其盐类,其中,
R3为:
(c1)氢原子;或
(c2)(C1-C6)烷基,
X1、X2、X3及X4分别独立地为:
(e1)氢原子;
(e2)卤素原子;或
(e7)(C1-C6)烷氧基,
Y为氧原子。
[4]一种农园艺用杀菌剂,其特征在于,
所述农园艺用杀菌剂含有所述[1]~[3]中任一项所述的化合物或其盐类作为有效成分。
[5]一种植物病害的防治方法,其特征在于,
利用有效量所述[4]所述的农园艺用杀菌剂处理植物或土壤。及
[6]一种所述[1]~[3]中任一项所述的化合物或其盐类作为农园艺用杀菌剂的应用。
发明效果
本发明的化合物或其盐类作为农园艺用杀菌剂具有优异的效果。
具体实施方式
下面,对在关于本发明的化合物的通式(I)的定义中所使用的术语进行说明。
“卤素”是指“卤素原子”,表示氯原子、溴原子、碘原子或氟原子。
“(C1-C6)烷基”表示直链或支链状的碳原子数1~6的烷基,例如:甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、叔戊基、新戊基、2,3-二甲基-丙基、1-乙基丙基、1-甲基丁基、2-甲基丁基、正己基、异己基、2-己基、3-己基、2-甲基戊基、3-甲基戊基、1,1,2-三甲基丙基、3,3-二甲基丁基等。
“(C2-C6)烯基”表示直链或支链状的碳原子数2~6的烯基,例如,乙烯基、烯丙基、异丙烯基、1-丁烯基、2-丁烯基、2-甲基-2-丙烯基、1-甲基-2-丙烯基、2-甲基-1-丙烯基、戊烯基、1-己烯基、3,3-二甲基-1-丁烯基等,“(C2-C6)炔基”表示直链或支链状的碳原子数2~6的炔基,例如,乙炔基、1-炔丙基、2-炔丙基、1-丁炔基、2-丁炔基、3-丁炔基、3-甲基-1-炔丙基、2-甲基-3-炔丙基、戊炔基、1-己炔基、3-甲基-1-丁炔基、3,3-二甲基-1-丁炔基等。
“(C3-C6)环烷基”表示碳原子数3~6的环状的烷基,例如,环丙基、环丁基、环戊基、环己基等,“(C1-C6)烷氧基”表示直链或支链状的碳原子数1~6的烷氧基,例如,甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、叔丁氧基、正戊氧基、异戊氧基、叔戊氧基、新戊氧基、2,3-二甲基丙氧基、1-乙基丙氧基、1-甲基丁氧基、正己氧基、异己氧基、1,1,2-三甲基丙氧基等。
“(C1-C6)烷基硫基”表示直链或支链状的碳原子数1~6的烷基硫基,例如,甲基硫基、乙基硫基、正丙基硫基、异丙基硫基、正丁基硫基、仲丁基硫基、叔丁基硫基、正戊基硫基、异戊基硫基、叔戊基硫基、新戊基硫基、2,3-二甲基-丙基硫基、1-乙基丙基硫基、1-甲基丁基硫基、正己基硫基、异己基硫基、1,1,2-三甲基丙基硫基等。
“(C1-C6)烷基亚磺酰基”表示直链或支链状的碳原子数1~6的烷基亚磺酰基,例如,甲基亚磺酰基、乙基亚磺酰基、正丙基亚磺酰基、异丙基亚磺酰基、正丁基亚磺酰基、仲丁基亚磺酰基、叔丁基亚磺酰基、正戊基亚磺酰基、异戊基亚磺酰基、叔戊基亚磺酰基、新戊基亚磺酰基、2,3-二甲基-丙基亚磺酰基、1-乙基丙基亚磺酰基、1-甲基丁基亚磺酰基、正己基亚磺酰基、异己基亚磺酰基、1,1,2-三甲基丙基亚磺酰基等。
“(C1-C6)烷基磺酰基”表示直链或支链状的碳原子数1~6的烷基磺酰基,例如,甲基磺酰基、乙基磺酰基、正丙基磺酰基、异丙基磺酰基、正丁基磺酰基、仲丁基磺酰基、叔丁基磺酰基、正戊基磺酰基、异戊基磺酰基、叔戊基磺酰基、新戊基磺酰基、2,3-二甲基-丙基磺酰基、1-乙基丙基磺酰基、1-甲基丁基磺酰基、正己基磺酰基、异己基磺酰基、1,1,2-三甲基丙基磺酰基等。
“(C1-C6)烷基羰基”表示碳原子数2~7的烷基羰基,例如,乙酰基、丙酰基、丁酰基、2-甲基丙酰基、戊酰基、2-甲基丁酰基、3-甲基丁酰基、新戊酰基、己酰基、环丙基羰基等具有所述(C1-C6)烷基的烷基羰基等。
“(C1-C6)烷氧基羰基”表示碳原子数2~7的烷氧基羰基,例如,甲氧基羰基、乙氧基羰基、正丙氧基羰基、异丙氧基羰基、正丁氧基羰基、异丁氧基羰基、仲丁氧基羰基、叔丁氧基羰基、戊氧基羰基等具有所述(C1-C6)烷氧基的烷氧基羰基等。
在上述“(C1-C6)烷基”、“(C2-C6)烯基”、“(C2-C6)炔基”、“(C3-C6)环烷基”、“(C1-C6)烷氧基”、“(C1-C6)烷基硫基”、“(C1-C6)烷基亚磺酰基”或“(C1-C6)烷基磺酰基”等基中,可以在每个基团的可取代的位置上取代1个或2个以上卤素原子,在取代的卤素原子为2个以上的情况下,卤素原子可以相同或不同。将在每个基团的可取代的位置上取代1个或2个以上卤素原子而得到的基团分别表示为“卤代(C1-C6)烷基”、“卤代(C2-C6)烯基”、“卤代(C2-C6)炔基”、“卤代(C3-C6)环烷基”、“卤代(C1-C6)烷氧基”、“卤代(C1-C6)烷基硫基”、“卤代(C1-C6)烷基亚磺酰基”或“卤代(C1-C6)烷基磺酰基”。
“(C1-C6)”、“(C2-C6)”、“(C3-C6)”等表记表示各种取代基的碳原子数的范围。而且,针对上述取代基所连接的基团,也能够应用上述定义,例如,“(C1-C6)烷氧基(C1-C6)烷基”表示该基团为直链或支链状的碳原子数1~6的烷氧基键合于直链或支链状的碳原子数1~6的烷基而成的基团。
“芳基基团(aryl group)”及“芳基(aryl)”表示碳原子数6~10的芳香族烃基,例如,苯基、萘基等。
“杂芳基基团”及“杂芳基”表示单环式芳香族杂环基,例如,呋喃基、噻吩基、吡啶基、嘧啶基、哒嗪基、吡嗪基、吡咯基、咪唑基、吡唑基、噻唑基、异噻唑基、噁唑基、异噁唑基、噁二唑基、噻二唑基、三唑基、四唑基、三嗪基等。
“环上具有1~2个氧原子的3元~6元非芳香族杂环基”表示非芳香族杂环基,例如,环氧乙烷基、氧杂环丁烷基、四氢呋喃基、四氢吡喃基、1,3-二氧杂环戊基、1,3-二噁烷基、1,4-二噁烷基等。
作为本发明的通式(I)表示的化合物的盐类,可示例与无机或有机的盐基的盐类,例如,盐酸盐、硫酸盐、硝酸盐、磷酸盐等无机酸盐类、醋酸盐、富马酸盐、马来酸盐、草酸盐、甲磺酸盐、苯磺酸盐、对甲苯磺酸盐等有机酸盐类、钠离子、钾离子、钙离子、三甲基铵等。
本发明的通式(I)表示的化合物及其盐类可能在其结构式中具有一个或多个不对称中心,还可能存在两种以上旋光异构体及非对映体,本发明包括每个旋光异构体及按照任意的比例包含这些旋光异构体的混合物。另外,本发明的通式(I)表示的化合物及其盐类也可能在其结构式中存在来自碳-碳双键的两种几何异构体,本发明包括每个几何异构体及按照任意的比例包含这些几何异构体的混合物。
在本发明的通式(I)表示的化合物中,下面,示出优选的方式。
作为R1,优选为:
(a2)(C1-C6)烷基。
作为R2,优选为:
(b1)氢原子。
作为R3,优选为:
(c1)氢原子;
(c2)(C1-C6)烷基;或
(c5)(C3-C6)环烷基,
进一步优选为:
(c1)氢原子;或
(c2)(C1-C6)烷基。
作为R4,优选为:
(d2)(C1-C6)烷基;
(d3)(C2-C6)烯基;
(d4)(C2-C6)炔基;
(d5)(C3-C6)环烷基;
(d6)(C1-C6)烷氧基;
(d7)卤代(C1-C6)烷基;
(d12)Ra(Rb)N基(式中,Ra及Rb分别独立地表示氢原子、(C1-C6)烷基、(C3-C6)环烷基、(C3-C6)环烷基(C1-C6)烷基、苯基、(C1-C6)烷基羰基或苯基羰基。);
(d13)芳基;
(d14)环上具有1~8个取代基的芳基,所述取代基分别独立地选自由卤素原子、氰基、硝基、(C1-C6)烷基、(C1-C6)烷氧基、(C3-C6)环烷基、卤代(C1-C6)烷基、卤代(C1-C6)烷氧基、卤代(C3-C6)环烷基、(C1-C6)烷基硫基、(C1-C6)烷基亚磺酰基、(C1-C6)烷基磺酰基、卤代(C1-C6)烷基硫基、卤代(C1-C6)烷基亚磺酰基及卤代(C1-C6)烷基磺酰基构成的组;
(d15)杂芳基;
(d17)芳基(C1-C6)烷基;
(d21)链上具有1~3个取代基的(C1-C6)烷基,所述取代基分别独立地选自由氰基、(C1-C6)烷氧基、Ra(Rb)N基(式中,Ra及Rb与所述相同。)、(C1-C6)烷基硫基、(C1-C6)烷基亚磺酰基及(C1-C6)烷基磺酰基构成的组;或
(d22)环状具有1~2个氧原子的3元~6元非芳香族杂环基。
作为X1、X2、X3及X4,优选分别独立地为:
(e1)氢原子;
(e2)卤素原子;
(e5)(C1-C6)烷基;
(e7)(C1-C6)烷氧基;
(e11)(C1-C6)烷基硫基;
(e12)(C1-C6)烷基亚磺酰基;或
(e13)(C1-C6)烷基磺酰基,
进一步优选分别独立地为:
(e1)氢原子;
(e2)卤素原子;或
(e7)(C1-C6)烷氧基。
作为Y,优选为氧原子;或硫原子,
进一步优选为氧原子。
本发明的各种化合物能够通过例如下述制造方法来制造,但本发明的化合物及其制造方法不限定于此。
制造方法1
【化学式2】
(式中,R1、R4、X1、X2、X3、X4及Y与针对所述式(I)所示的基团相同。)
在本发明的化合物中,通式(I-1)表示的化合物能够通过上述方案中所示的下述工序[a]来制造。
工序[a]使通式(1)表示的化合物与通式(2)表示的化合物及通式(3)表示的化合物反应,从而制造通式(I-1)表示的化合物。
工序[a]
在惰性溶剂存在下,使能够通过国际公开第2017/055473号小册子中记载的方法制造的通式(1)表示的化合物,与通式(2)表示的化合物及通式(3)表示的化合物反应,从而能够制造通式(I-1)表示的化合物。
作为能够在本反应(工序[a])中使用的通式(3)表示的化合物,例如,可列举:甲醇钛(IV)、乙醇钛(IV)、正丙醇钛(IV)、异丙醇钛(IV)、正丁醇钛(IV)、及叔丁醇钛(IV)等,作为其使用量,相对于通式(1)表示的化合物通常从1倍摩尔~5倍摩尔的范围中适当选择即可。
作为本反应(工序[a])中使用的惰性溶剂,只要为不会显著抑制本反应的进行的物质即可,例如,可示例:戊烷、己烷、环己烷等脂肪族烃类、苯、甲苯、及二甲苯等芳香族烃类;二氯甲烷、氯仿、及四氯化碳等卤化烃类;氯苯、及二氯苯等卤化芳香族烃类;醋酸乙酯、及醋酸丙酯等酯类;乙腈、及丙腈等腈类;二甲基甲酰胺、及二甲基乙酰胺等酰胺类;丙酮、及甲乙酮等酮类;以及二甲基亚砜、及1,3-二甲基-2-咪唑啉酮等非质子性极性溶剂等惰性溶剂,这些惰性溶剂能够单独使用或混合使用2种以上。作为其使用量,相对于通式(1)表示的化合物1摩尔通常从0.1~100L的范围中适当选择即可。
本反应为等摩尔反应,因此等摩尔使用各反应剂即可,但也能够过量使用任意的反应剂。作为反应温度,通常在室温至所使用的惰性溶剂的沸点的范围内进行反应,反应时间根据反应规模、反应温度而不同,通常在数分~48小时的范围进行反应即可。反应结束后,通过常规方法从包含目标物的反应系统中分离目标物即可,可以根据需要通过重结晶、柱层析等进行精制,从而得到目标物。
制造方法2
【化学式3】
(式中,R1、R3、R4、X1、X2、X3、X4及Y与针对所述式(I)所示相同,L表示卤素原子、甲磺酰基、甲苯磺酰基、三氟甲磺酸酯基等离去基团。)
在本发明的化合物中,通式(I-2)表示的化合物能够通过上述方案所示的下述工序[b]至[e]来制造。
工序[b]使通式(4)表示的化合物与通式(2)表示的化合物及通式(3)表示的化合物反应,从而制造通式(5)表示的化合物。
工序[c]使通式(5)表示的化合物与通式(6)表示的化合物反应,从而制造通式(7)表示的化合物。
工序[d]使通式(7)表示的化合物与羟基胺(8)反应,从而制造通式(9)表示的化合物。
工序[e]使通式(9)表示的化合物与三氟醋酸酐(10)反应,从而制造通式(I-2)表示的化合物。
工序[b]
在惰性溶剂存在下,使通式(4)表示的化合物与通式(2)表示的化合物及通式(3)表示的化合物反应,从而能够制造通式(5)表示的化合物。
作为能够在本反应中使用的通式(3)表示的化合物,例如,可列举:甲醇钛(IV)、乙醇钛(IV)、正丙醇钛(IV)、异丙醇钛(IV)、正丁醇钛(IV)、叔丁醇钛(IV)等,作为其的使用量,相对于通式(4)表示的化合物通常从1倍摩尔~5倍摩尔的范围中适当选择即可。
作为本反应中使用的惰性溶剂,只要为不会显著抑制本反应的进行的物质即可,例如,可示例:戊烷、己烷、及环己烷等链状或环状的脂肪族烃类;苯、甲苯、及二甲苯等芳香族烃类;二氯甲烷、氯仿、及四氯化碳等卤化烃类;氯苯、及二氯苯等卤化芳香族烃类;醋酸乙酯、及醋酸丙酯等酯类;乙腈、丙腈等腈类;二甲基甲酰胺、及二甲基乙酰胺等酰胺类;丙酮、及甲乙酮等酮类;以及二甲基亚砜、及1,3-二甲基-2-咪唑啉酮等非质子性极性溶剂等惰性溶剂,这些惰性溶剂能够单独使用或混合使用2种以上。作为其使用量,相对于通式(4)表示的化合物1摩尔通常从0.1~100L的范围中适当选择即可。
本反应为等摩尔反应,因此等摩尔使用各反应剂即可,但也能够过量使用任意的反应剂。作为反应温度,通常在室温至所使用的惰性溶剂的沸点的范围内进行反应,反应时间根据反应规模、反应温度而不同,通常在数分~48小时的范围进行反应即可。反应结束后,通过常规方法从包含目标物的反应系统中分离目标物即可,可以根据需要通过重结晶、柱层析等进行精制,从而得到目标物。
工序[c]
在碱及惰性溶剂存在下,使通式(5)表示的化合物与通式(6)表示的化合物反应,从而能够制造通式(7)表示的化合物。
作为能够在本反应中使用的碱,例如,可示例:氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、碳酸氢钠、及碳酸氢钾等无机碱类;氢化钠、及氢化钾等碱金属氢化物类;叔丁醇钾、甲醇钠、及乙醇钠等碱金属醇盐类;三乙基胺、二异丙基乙基胺、及1,8-二氮杂双环[5.4.0]十一-7-烯等叔胺类;以及吡啶、及二甲基-氨基吡啶等含氮芳香族化合物等,作为其使用量,相对于通式(5)表示的化合物通常从1倍摩尔~5倍摩尔的范围中适当选择即可。
作为本反应中使用的惰性溶剂,只要为不会显著抑制本反应的进行的物质即可,例如,可示例:苯、甲苯、及二甲苯等芳香族烃类;二氯甲烷、氯仿、及四氯化碳等卤化烃类;氯苯、及二氯苯等卤化芳香族烃类;二乙基醚、甲基叔丁基醚、二噁烷、及四氢呋喃等链状或环状醚类;醋酸乙酯等酯类、二甲基甲酰胺、及二甲基乙酰胺等酰胺类;丙酮、及甲乙酮等酮类;以及二甲基亚砜、及1,3-二甲基-2-咪唑啉酮等非质子性极性溶剂等惰性溶剂,这些惰性溶剂能够单独使用或混合使用2种以上。作为其的使用量,相对于通式(5)表示的化合物1摩尔通常从0.1~100L的范围中适当选择即可。
本反应为等摩尔反应,因此等摩尔使用各反应剂即可,但也能够过量使用任意的反应剂。作为反应温度,通常在室温至所使用的惰性溶剂的沸点的范围内进行反应,反应时间依赖于反应规模、反应温度,通常在数分~48小时的范围进行反应即可。反应结束后,通过常规方法从包含目标物的反应系统中分离目标物即可,能够根据需要通过重结晶、柱层析等进行精制,从而得到目标物。
工序[d]
在惰性溶剂存在下,使通式(7)表示的化合物与羟基胺盐酸盐(8)反应,从而能够制造通式(9)表示的化合物。
作为本反应中使用的惰性溶剂,只要为不会显著抑制本反应的进行的物质即可,例如,可示例:甲醇、乙醇、1-丙醇、及2-丙醇等醇类;二乙基醚、甲基叔丁基醚、二噁烷、及四氢呋喃等链状或环状醚类;二甲基甲酰胺、及二甲基乙酰胺等酰胺类;二甲基亚砜、及1,3-二甲基-2-咪唑啉酮等非质子性极性溶剂;以及水等惰性溶剂,这些惰性溶剂能够单独使用或混合使用2种以上。作为其的使用量,相对于通式(7)表示的化合物1摩尔通常从0.1~100L的范围中适当选择即可。
本反应为等摩尔反应,因此等摩尔使用各反应剂即可,但也能够过量使用任意的反应剂。作为反应温度,通常在室温至所使用的惰性溶剂的沸点的范围内进行反应,反应时间根据反应规模、反应温度而不同,通常在数分~48小时的范围进行反应即可。反应结束后,通过常规方法从包含目标物的反应系统中分离目标物即可,可以根据需要通过重结晶、柱层析等进行精制,从而制造目标物。
工序[e]
在碱及惰性溶剂存在下,使通式(9)表示的化合物与三氟醋酸酐(10)反应,从而能够制造通式(I-2)表示的化合物。
作为能够在本反应中使用的碱,例如,可示例:碳酸钠、碳酸钾、碳酸氢钠、及碳酸氢钾等无机碱类;三乙基胺、二异丙基乙基胺、及1,8-二氮杂双环[5.4.0]十一-7-烯等叔胺类;以及吡啶、及二甲基-氨基吡啶等含氮芳香族化合物等,作为其的使用量,相对于通式(9)表示的化合物通常从1倍摩尔~5倍摩尔的范围中适当选择即可。
作为能够在本反应中使用的惰性溶剂,只要为不会显著抑制本反应的进行的物质即可,例如,可示例:苯、甲苯、及二甲苯等芳香族烃类;二氯甲烷、氯仿、及四氯化碳等卤化烃类;氯苯、及二氯苯等卤化芳香族烃类;二乙基醚、甲基叔丁基醚、二噁烷、及四氢呋喃等链状或环状醚类;醋酸乙酯等酯类;二甲基甲酰胺、及二甲基乙酰胺等酰胺类;丙酮、及甲乙酮等酮类;以及二甲基亚砜、及1,3-二甲基-2-咪唑啉酮等非质子性极性溶剂等惰性溶剂,这些惰性溶剂能够单独使用或混合使用2种以上。作为其的使用量,相对于通式(9)表示的化合物1摩尔通常从0.1~100L的范围中适当选择即可。
本反应为等摩尔反应,因此等摩尔使用各反应剂即可,但也能够过量使用任意的反应剂。作为反应温度,通常在室温至所使用的惰性溶剂的沸点的范围内进行反应,反应时间根据反应规模、反应温度而不同,通常在数分~48小时的范围进行反应即可。反应结束后,通过常规方法从包含目标物的反应系统中分离目标物即可,可以根据需要通过重结晶、柱层析等进行精制,从而制造目标物。
制造方法3
【化学式4】
(式中,R1、R4、X2、X3、X4及Y与针对所述式(I)所示的基团相同、R5表示(C1-C6)烷基,n表示1~2的整数。)
在本发明的化合物中,通式(I-3)及(I-4)表示的化合物能够分别通过上述方案所示的下述工序[f]至[g]、及工序[f]至[h]来制造。
工序[f]使通式(1-2)表示的化合物与通式(10)表示的化合物反应,从而制造通式(1-3)表示的化合物。
工序[g]使通式(1-3)表示的化合物与通式(3)表示的化合物及通式(2)表示的化合物反应,从而制造通式(I-3)表示的化合物。
工序[h]氧化通式(I-3)表示的化合物,从而制造通式(I-4)表示的化合物。
工序[f]
在惰性溶剂存在下,使通式(1-2)表示的化合物与通式(10)表示的化合物反应,从而能够制造通式(1-3)表示的化合物。
作为在本反应中使用的惰性溶剂,只要为不会显著抑制本反应的进行的物质即可,例如,可示例:苯、甲苯、及二甲苯等芳香族烃类;氯苯、及二氯苯等卤化芳香族烃类;二乙基醚、甲基叔丁基醚、二噁烷、及四氢呋喃等链状或环状醚类;二甲基甲酰胺、及二甲基乙酰胺等酰胺类;丙酮、及甲乙酮等酮类;以及二甲基亚砜、及1,3-二甲基-2-咪唑啉酮等非质子性极性溶剂等惰性溶剂,这些惰性溶剂能够单独使用或混合使用2种以上。作为其的使用量,相对于通式(1-2)表示的化合物1摩尔通常从0.1~100L的范围中适当选择即可。
本反应为等摩尔反应,因此等摩尔使用各反应剂即可,但也能够过量使用任意的反应剂。作为反应温度,通常在室温至所使用的惰性溶剂的沸点的范围内进行反应,反应时间根据反应规模、反应温度而不同,通常在数分~48小时的范围进行反应即可。反应结束后,通过常规方法从包含目标物的反应系统中分离目标物即可,可以根据需要通过重结晶、柱层析等进行精制,从而制造目标物。
工序[g]
按照所述制造方法1的工序[a]中记载的方法,使通式(1-3)表示的化合物与通式(2)表示的化合物及通式(3)表示的化合物反应,从而能够制造通式(I-3)表示的化合物。
工序[h]
通过化学合成中常用的方法氧化通式(I-3)表示的化合物,从而能够制造通式(I-4)表示的化合物。
以下将在第1表中示例本发明的通式(I)表示的化合物的代表例,但本发明不现定于此。
表中,“Me”表示甲基,“Et”表示乙基,“n-Pr”表示正丙基,“i-Pr”表示异丙基,“c-Pr”表示环丙基,“n-Bu”表示正丁基,“i-Bu”表示异丁基,“s-Bu”表示仲丁基,“t-Bu”表示叔丁基,“c-Pen”表示环戊基,“Ph”表示苯基。物性表示熔点(℃)或折射率nD(测定温度)。
【化学式5】
【表1】
表1
【表2】
接表1
【表3】
接表1
【表4】
接表1
【表5】
接表1
【表6】
接表1
1)低极性非对映体(Rf值高):化合物编号135及化合物编号138
2)高极性非对映体(Rf值低):化合物编号136及化合物编号139
【表7】
接表1
含有本发明的通式(I)表示的化合物或其盐类作为有效成分的农园艺用杀菌剂适合谷物类、果树、蔬菜、其它作物及花卉类产生的病害的防治。
作为对象病害,可列举:丝状菌类疾病、细菌疾病和病毒性疾病。作为丝状菌类病害,例如,可列举:由不完全菌类导致的病害(例如,葡萄孢(Botrytis)属病害、长蠕孢(Helminthosporium)属病害、镰刀菌(Fusarium)属病害、壳针孢(Septoria)属病害、尾孢(Cercospora)属病害、假孢子菌(Pseudocercosporella)属病害、喙孢(Rhynchosporium)属病害、梨孢(Pyricularia)属病害、链格孢(Alternaria)属病害等)、担子菌类(例如,海弥列担子菌(Hemilelia)属病害、丝核菌属(Rhizoctonia)属病害、黑粉菌(Ustilago)属病害、核瑚菌(Typhula)属病害、及柄锈菌(Puccinia)属病害等)、子囊菌类导致的病害(例如,黑星菌(Venturia)属病害、足球菌(Podosphaera)属病害、小球腔菌(Leptosphaeria)属病害、布氏白粉(Blumeria)属病害、白粉菌(Erysiphe)属病害、微座孢(Microdochium)属病害、核盘菌(Sclerotinia)属病害、禾顶囊壳(Gaeumannomyces)属病害、链核盘菌属(Monilinia)属病害、钩丝壳(Unsinula)属病害等)、其他菌类(例如,壳二孢(Ascochyta)属病害、茎点霉(Phoma)属病害、腐霉菌(Pythium)属病害、伏革菌(Corticium)属病害、核腔菌(Pyrenophora)属病害等)。作为细菌类病害,例如,可列举:假单胞菌(Pseudomonas)属病害、黄单胞菌(Xanthomonas)属病害、及欧文氏菌(Erwinia)属病害等。作为病毒病害,可列举:例如烟草花叶病毒(Tabacco mosaic virus)等导致的病害等。
作为丝状菌类病害的具体病害,例如,可列举:稻瘟病(Pyriculariaoryzae)、水稻纹枯病(Rhizoctonia solani)、水稻胡麻叶枯病(Cochiobolusmiyabeanus)、水稻苗立枯病(Rhizopus chinensis、Pythium graminicola、Fusarium graminicola、Fusarium roseum、Mucor sp.、Phoma sp.、Tricoderma sp.)、水稻恶苗病(Gibberellafujikuroi)、大麦及小麦等的白粉病(Blumeriagraminis)、黄瓜等的白粉病(Sphaerothecafuliginea)、茄子等的白粉病(Erysiphe cichoracoarum)及其它宿主植物的白粉病、大麦及小麦等的眼斑病(Pseudocercosporellaherpotrichoides)、小麦等的黑穂病(Urocystistritici)、大麦及小麦等的雪腐病(Microdochiumnivalis、Pythium iwayamai、Typhlaishikariensis、Typhlaincarnata、Sclerotinia borealis)、大麦及小麦等的赤霉病(Fusariumgraminearum、Fusarium avenaceum、Fusarium culmorum、Microdochiumnivalis)、大麦及小麦等的锈病(Puccinia recondita、Puccinia striiformis、Puccinia graminis)、大麦及小麦等的立枯病(Gaeumannomycesgraminis)、燕麦冠锈病(Puccinia coronata)、黄豆的锈病(Phakopsorapachyrhizi)及其它植物的锈病、黄瓜及草莓等的灰霉病(Botrytiscinerea)、番茄及卷心菜等的菌核病(Sclerotiniasclerotiorum)、土豆及番茄等的晚疫病(Phytophthora infestans);以及,作为其它植物的晚疫病,可列举:黄瓜黑星病(Pseudoperonosporacubensis)、葡萄黑星病(Plasmoparaviticola)等各种植物的黑星病、苹果黑星病(Venturia inaequalis)、苹果斑点落叶病(Alternaria mali)、茄子黑斑病(Alternaria kikuchiana)、柑橘黑点病(Diaporthecitri)、柑橘疮痂病(Elsinoefawcetti)、甜菜褐斑病(Cercosporabeticola)、花生褐斑病(Cercosporaarachidicola)、花生黑斑病(Cercosporapersonata)、小麦叶枯病(Septoriatritici)、小麦颖枯病(Leptosphaeria nodorum)、大麦网纹病(Pyrenophora teres)、大麦斑叶病(Pyrenophoragraminea)、大麦云纹病(Rhynchosporiumsecalis)、大麦散黑穗病(Ustilago nuda)、小麦网腥黑穗病(Tilletia caries)、草坪叶腐病(Rhizoctoniasolani)、以及草坪币斑病(Sclerotiniahomoeocarpa)等。
作为细菌类病害的具体的病害,可列举:由假单胞菌(Pseudomonas)属引起的、例如黄瓜斑点细菌病(Pseudomonas syringaepv.lachrymans)、番茄青枯病(Pseudomonassolanacearum)及水稻细菌性谷枯病(Pseudomonas glumae);由Xanthomonas属引起的、例如卷心菜黑腐病(Xanthomonas campestris)、水稻白叶枯病(Xanthomonas oryzae)及柑橘溃疡病(Xanthomonas citri);以及由欧文氏菌(Erwinia)属引起的、例如卷心菜软腐病(Erwinia carotovora)等。
能够使用本发明的通式(I)表示的化合物或其盐类的有用植物不作特别限定,例如,可列举:谷物类(例如,水稻、大麦、小麦、黑麦、燕麦、玉米等)、豆类(黄豆、红豆、蚕豆、豌豆、绿豆、花生等)、果树-果实类(苹果、柑橘类、梨、葡萄、桃、梅、樱桃、核桃、栗子、杏子、橡胶等)、叶菜及果菜类(卷心菜、番茄、菠菜、西兰花、生菜、洋葱、葱(细香葱、大葱)、青椒、茄子、草莓、辣椒、秋葵、韭葱等)、根菜类(胡萝卜、土豆、甘薯、芋头、白萝卜、芜菁、莲藕、牛蒡、大蒜、辣韭等)、加工用作物(棉花棉、麻、甜菜、啤酒花、甘蔗、甜菜、橄榄、橡胶、咖啡、烟草、茶等)、瓜类(南瓜、黄瓜、西瓜、香瓜、甜瓜等)、牧草类(果树草、高粱、猫尾草、苜蓿草、紫花苜蓿等)、草坪类(高丽草坪、剪股颖等)、香料等观赏用作物(薰衣草、迷迭香、百里香、欧芹、胡椒、生姜等)、花卉类(菊花、玫瑰花、康乃馨、兰花、郁金香、百合等)、庭木(银杏、樱花类、青木等)、及林木(库页冷杉类、鱼鳞云杉类、松类、丝柏、日本雪松、日本扁柏、桉树等)等植物。
上述“植物”中也包含通过经典的育种法、或者基因重组技术被赋予了对于异恶唑草酮等HPPD抑制剂;咪唑乙烟酸、及噻吩磺隆等ALS抑制剂;草甘膦等EPSP合成酶抑制剂;草铵膦等谷氨酰胺合成酶抑制剂;烯禾啶等乙酰基CoA羧化酶抑制剂;溴苯腈、麦草畏、以及2,4-D等除草剂的耐药性的植物。
作为通过经典的育种法被赋予了耐药性的“植物”的例子,具有:对于咪唑乙烟酸等咪唑啉酮类ALS抑制型除草剂具有耐药性的油菜、小麦、向日葵、水稻,它们已经以Clearfield(注册商标)的商品名被销售。具有通过经典的育种法对噻吩磺隆等磺酰基尿素类ALS抑制型除草剂具有耐药性的黄豆,它已经以STS黄豆的商品名销售。作为同样通过经典的育种法被赋予了对于三酮肟类、芳氧基苯氧基丙酸类除草剂等乙酰基CoA羧化酶抑制剂的耐药性的植物的例子,具有SR玉米等。
另外,被赋予了对于乙酰基CoA羧化酶抑制剂的耐药性的植物记载于美国国家科学院院刊(Proc.Natl.Acad.Sci.USA)87卷,7175~7179页(1990年)等。另外,杂草学会(Weed Science)53卷,728~746页(2005年)等中报道了对乙酰基CoA羧化酶抑制剂具有耐药性的变异乙酰基CoA羧化酶,通过利用基因重组技术将这种变异乙酰基CoA羧化酶基因导入植物中或者将与赋予抵抗性相关的变异导入植物乙酰基CoA羧化酶中,能够制得对于乙酰基CoA羧化酶抑制剂具有耐药性的植物,而且,将以嵌合修复技术(GuraT.1999.Repairing the Genome’s Spelling Mistakes.Science 285:316-318.)为代表的碱基取代变异导入核酸导入植物细胞内,从而在植物的乙酰基CoA羧化酶基因或ALS基因等导入位点特异性氨基酸取代变异,由此能够制得对于乙酰基CoA羧化酶抑制剂或ALS抑制剂等具有耐药性的植物,这些植物也能够使用本发明的通式(I)表示的化合物或其盐类。
进而,作为在基因重组植物中表达的毒素,可列举:来自蜡样芽孢杆菌或乳状芽孢杆菌的杀虫性蛋白质;来自苏云金芽胞杆菌的Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1或Cry9C等δ-内毒素;VIP1、VIP2、VIP3或VIP3A等杀虫蛋白质;来自线虫的杀虫蛋白质;蝎毒素、蜘蛛毒素、蜜蜂毒素或昆虫特异性神经毒素等由动物产生的毒素;丝状菌类毒素;植物凝集素;凝集素;胰蛋白酶抑制剂、丝氨酸蛋白酶抑制剂、马铃薯糖蛋白、胱抑素、木瓜蛋白酶抑制剂等蛋白酶抑制剂;赖氨酸、玉米-RIP、相思子毒素、丝瓜素、皂草素、Briodin等核糖体灭活蛋白质(RIP);3-羟基类固醇氧化酶、蜕皮激素-UDP-葡萄糖基转移酶、胆固醇氧化酶等类固醇代谢酶;蜕皮激素抑制剂;HMG-CoA还原酶;钠通道、钙通道抑制剂等离子通道抑制剂;保幼激素酯酶;利尿激素受体;二苯乙烯合酶;联苄合酶;几丁质酶;葡聚糖酶等。
另外,作为这种在基因重组植物中表达的毒素,也包含Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1、Cry9C、Cry34Ab或Cry35Ab等δ-内毒素蛋白质;VIP1、VIP2、VIP3或VIP3A等杀虫蛋白质的混合毒素;缺失了一部分的毒素;被修饰的毒素。混合毒素使用重组技术通过这些蛋白质的不同结构域的新的组合而制得。作为缺失了一部分的毒素,已知有缺失了部分氨基酸序列的Cry1Ab。在被修饰的毒素中,天然型毒素的氨基酸的一个或多个被取代。
EP-A-0 374 753、WO 93/07278、WO 95/34656、EP-A-0 427 529、EP-A-451 878、WO03/052073等中记载有这些毒素的例子及能够合成这些毒素的重组植物。
本发明的农园艺用杀菌剂也可以与这些技术并用或者与这些技术形成体系。
为了防治各种病害,将本发明的农园艺用杀菌剂按照病害防治的有效量直接或以用水等适当稀释或者悬浮的形式用于预测会产生该病害的植物即可,例如,对于在果树、谷物类、蔬菜等中产生的病害,除向茎叶部散布之外,也可以进行种子药剂浸渍、种子粉衣、Calper处理等种子处理;对土壤等进行处理从根部使其吸收使用,例如,土壤全层混和、行道施药、苗床土壤混和、穴盘苗处理、种植穴处理、植株基部处理、追肥、水稻苗箱处理、水面施药等。此外,也可以向营养液(水耕)栽培中的营养液施药、进行熏烟或者进行树干注射等。
而且,将本发明的农园艺用杀菌剂按照病害防治的有效量直接或以用水等适当稀释或者悬浮的形式用于预测会产生该病害的场所即可。
作为种子处理的方法,例如,可列举:稀释或不稀释液状或固体状的制剂,并在液体状态下浸渍种子以使药剂浸透的方法、将固形制剂或液状制剂与种子混和,以进行粉衣处理使其附着于种子的表面的方法、与树脂、聚合物等附着性载体混和并涂布于种子的方法、种植的同时散布在种子附近的方法等。
进行该种子处理的“种子”表示用于植物的繁殖的栽培初期的植物体,例如,除种子之外,还可列举:球根、块茎、种薯、株芽、繁殖芽、鳞茎、或者用于扦插栽培的营养繁殖用植物体。
在实施本发明的使用方法的情况下,植物的“土壤”或“栽培载体”表示用于栽培作物的支撑体,特别是生根的支撑体,材质不作特别制限,只要是植物能够生长发育的材质即可,可以为所谓的土壤、育苗垫、水等,作为具体的素材,例如,可以为砂子、浮石、蛭石、硅藻土、琼脂、凝胶状物质、高分子物质、岩棉、玻璃棉、木片、树皮等。
作为向作物茎叶部等散布的方法,可列举:将乳剂、浓悬浊剂等液体制剂或可湿性粉剂或者水分散性颗粒剂等固形制剂用水适当稀释后散布的方法、散布粉剂的方法、或熏烟等。
作为向土壤施药的方法,例如,可列举:将液体制剂用水稀释或不稀释,并施药于植物体的植株基部或育苗用苗床等的方法、将粒剂散布于植物体的植株基部或用于育苗的苗床等的方法、播种前或移植前散布粉剂、可湿性粉剂、水分散性颗粒剂、粒剂等并与土壤整体的方法、播种前或栽植植物体前在种植穴、行道等上散布粉剂、可湿性粉剂、水分散性颗粒剂、粒剂等的方法等。
作为向水稻的育苗箱施药的方法,剂型根据例如播种时施药、绿化期施药、移植时施药等施药时段的不同而不同,但以粉剂、水分散性颗粒剂、粒剂等剂型施药即可。也可以通过与培土混和来施药,能够将培土与粉剂、水分散性颗粒剂或粒剂等混和,例如,与苗床土壤混和、与覆土混和、与培土整体混和等。也可以简单地将培土和各种制剂交替制成层状来施药。
作为向水田施药的方法,通常,将大粒(jumbo)剂、袋剂、粒剂、水分散性颗粒剂等固形制剂、浓悬浊剂(フロアブル)、乳剂等液体状制剂散布于淹水状态的水田。另外,也可以在插秧时将适当的制剂直接或者与肥料混和后散布或注入土壤中。另外,也可以通过出水口、灌溉装置等向水田流入水的源头使用乳剂、浓悬浊剂等药液,从而随着供水简便地施药。
对于旱田作物,能够在播种至育苗期对种子或靠近植物体的栽培载体等进行处理。对于直接播种于旱田的植物,除对种子直接处理之外,优选对正在栽培的植物的植株基部进行处理。例如,能够使用粒剂进行散布处理、或将稀释或者未稀释在水的药剂以液状进行灌溉处理。将粒剂与播种前的栽培载体混和之后进行播种也是一种优选的处理。
作为进行移植的栽培植物的播种、育苗期的处理,除对种子进行直接处理之外,优选对育苗用苗床进行制成液状的药剂的灌溉处理或粒剂的散布处理。另外,定植时用粒剂对种植穴进行处理或将粒剂与移植场所附近的栽培载体混和也是优选的处理。
本发明的通式(I)表示的化合物或其盐类通常按照农药制剂上常规方法制成方便使用的形状后使用。
即,作为本发明的通式(I)表示的化合物或其盐类,将其与适当的惰性载体或根据需要使用的辅助剂一起按照适当的比例进行配合,然后进行溶解、分离、悬浮、混合、含浸、吸附或者附着,从而制成适当的剂型,例如悬浮剂(浓悬浊剂)、乳剂、油剂、液剂、可湿性粉剂、水分散性颗粒剂、粒剂、粉剂、片剂、袋剂、大粒剂、悬乳剂等后使用即可。
除有效成分之外,本发明的农园艺用杀菌剂还可以根据需要含有通常用于农药制剂的添加成分。作为该添加成分,可列举:固体载体、液体载体等载体、表面活性剂、分散剂、湿润剂、粘合剂、粘着赋予剂、增粘剂、着色剂、扩展剂、展着剂、防冻剂、抗结块剂、崩解剂、分解抑制剂等。此外,还可以根据需要在添加成分中使用防腐剂、植物片等。这些添加成分可以单独使用,另外,也可以组合使用两种以上。
作为固体载体,例如,可列举:石英、粘土、高岭石、叶蜡石、绢云母、滑石、膨润土、酸性黏土、凹凸棒石、沸石、硅藻土等天然矿物类、碳酸钙、硫酸铵、硫酸钠、氯化钾等无机盐类;合成硅酸、合成硅酸盐、淀粉、纤维素、植物粉末(例如锯末、椰子壳、玉米芯、烟梗等)等有机固体载体;聚乙烯、聚丙烯、聚偏二氯乙烯等塑料载体、尿素、无机中空体、塑料中空体、及气相法二氧化硅(fumed silica,白炭黑)等。它们可以单独使用,另外,也可以组合使用两种以上。
作为液体载体,例如,可列举:甲醇、乙醇、丙醇、异丙醇、及丁醇等一元醇类、乙二醇、二乙二醇、丙二醇、己二醇、聚乙二醇、聚丙二醇、甘油等多元醇类那样的醇类、丙二醇醚等多元醇化合物类;丙酮、甲乙酮、甲基异丁基酮、二异丁基酮、及环己酮等酮类;乙基醚、二噁烷、乙二醇单乙基醚、及二丙基醚、THF等醚类;正链烷烃、环烷、异构烷烃、煤油、及矿物油等脂肪族烃类;苯、甲苯、二甲苯、溶剂石脑油、及烷基萘等芳香族烃类;二氯甲烷、氯仿、及四氯化碳等卤化烃类;醋酸乙酯、二异丙基邻苯二甲酸酯、二丁基邻苯二甲酸酯、二辛基邻苯二甲酸酯、及己二酸二甲酯等酯类;γ-丁内酯等内酯类;二甲基甲酰胺、二乙基甲酰胺、二甲基乙酰胺、及N-烷基吡咯烷酮等酰胺类;乙腈等腈类;二甲基亚砜等硫化合物类;黄豆油、油菜油、棉籽油、及蓖麻油等植物油;以及水等。它们可以单独使用,另外,也可以组合使用两种以上。
作为用作分散剂或湿展剂的表面活性剂,例如,可列举:失水山梨醇脂肪酸酯、聚氧乙烯失水山梨醇脂肪酸酯、蔗糖脂肪酸酯、聚氧乙烯脂肪酸酯、聚氧乙烯树脂酸酯、聚氧乙烯脂肪酸二酯、聚氧乙烯烷基醚、聚氧乙烯烷基芳基醚、聚氧乙烯烷基苯基醚、聚氧乙烯二烷基苯基醚、聚氧乙烯烷基苯基醚福尔马林缩合物、聚氧乙烯聚氧丙烯嵌段共聚物、聚苯乙烯聚氧乙烯嵌段聚合物、烷基聚氧乙烯聚丙烯嵌段共聚物醚、聚氧乙烯烷基胺、聚氧乙烯脂肪酸酰胺、聚氧乙烯脂肪酸联苯醚、聚亚烷基苄基苯基醚、聚氧亚烷基苯乙烯基苯基醚、乙炔二醇、聚氧亚烷基加成乙炔二醇、聚氧乙烯醚型有机硅、酯型有机硅、氟类表面活性剂、聚氧乙烯蓖麻油、聚氧乙烯硬化蓖麻油等非离子型表面活性剂、烷基硫酸盐、聚氧乙烯烷基醚硫酸盐、聚氧乙烯烷基苯基醚硫酸盐、聚氧乙烯苯乙烯基苯基醚硫酸盐、烷基苯磺酸盐、烷基芳基磺酸盐、木质素磺酸盐、烷基磺基琥珀酸盐、萘磺酸盐、烷基萘磺酸盐、萘磺酸的福尔马林缩合物的盐、烷基萘磺酸的福尔马林缩合物的盐、脂肪酸盐、多元羧酸盐、聚丙烯酸盐、N-甲基-脂肪酸肌氨酸盐、树脂酸盐、聚氧乙烯烷基醚磷酸盐、及聚氧乙烯烷基苯基醚磷酸盐等阴离子型表面活性剂;月桂胺盐酸盐、硬脂基丙基胺盐酸盐、油胺盐酸盐、硬脂基胺醋酸盐、硬脂基氨基丙基胺醋酸盐、烷基三甲基铵氯化物、及烷基二甲基-苯扎氯铵氯化物等烷基胺盐等阳离子表面活性剂;以及氨基酸型或甜菜碱型等两个性表面活性剂等。这些表面活性剂可以单独使用,另外,也可以组合使用两种以上。
作为粘合剂或粘着赋予剂,例如,可列举:羧甲基纤维素及其盐、糊精、水溶性淀粉、黄原胶、瓜尔胶、蔗糖、聚乙烯基吡咯烷酮、阿拉伯胶、聚乙烯基醇、聚乙烯基醋酸酯、聚丙烯酸钠、平均分子量6000~20000的聚乙二醇、平均分子量10万~500万的聚环氧乙烷、磷脂质(例如脑磷脂、卵磷脂等)纤维素粉末、糊精、加工淀粉、聚氨基羧酸螯合化合物、交联聚乙烯基吡咯烷酮、马来酸与苯乙烯类的共聚物、(甲基)丙烯酸类共聚物、由多元醇构成的聚合物与二羧酸酐的半酯、聚苯乙烯磺酸的水溶性盐、石蜡、萜烯、聚酰胺树脂、聚丙烯酸盐、聚氧乙烯、蜡、聚乙烯基烷基醚、烷基苯酚福尔马林缩合物、及合成树脂乳液等。
作为增粘剂,例如,可列举:黄原胶、瓜尔胶、定优胶(Diutan gum)、羧甲基纤维素、聚乙烯基吡咯烷酮、羧基乙烯基聚合物、丙烯酸类聚合物、淀粉化合物、及多糖类之类的水溶性高分子、以及高纯度膨润土、及气相法二氧化硅(fumed silica,白炭黑)之类的无机微粉等。
作为着色剂,例如,可列举:氧化铁、二氧化钛、普鲁士蓝之类的无机颜料;以及茜素染料、偶氮染料、金属酞菁染料之类的有机染料等。
作为防冻剂,例如,可列举:乙二醇、二乙二醇、丙二醇、甘油等多元醇类等。
作为防止结块或促进崩解的辅助剂,例如,可列举:淀粉、海藻酸、甘露糖、及半乳糖等多糖类;聚乙烯基吡咯烷酮、气相法二氧化硅(fumed silica,白炭黑)、酯胶、石油树脂、三聚磷酸钠、六偏磷酸钠、硬脂酸金属盐、纤维素粉末、糊精、甲基丙烯酸的共聚物、聚乙烯基吡咯烷酮、聚氨基羧酸螯合化合物、磺化苯乙烯-异丁烯-马来酸酐共聚物、以及淀粉-聚丙烯腈接枝共聚物等。
作为分解抑制剂,例如,可列举:沸石、生石灰、及氧化镁之类的干燥剂;苯酚化合物、胺化合物、硫化合物、及磷酸化合物等抗氧化剂;以及水杨酸化合物、及二苯甲酮化合物等紫外线吸收剂等。
作为防腐剂,例如,可列举山梨酸钾、1,2-苯并噻唑啉-3-酮等。
也可以根据需要进一步使用功能性展着剂、胡椒基丁醚等代谢分解抑制剂等活性增强剂、丙二醇等防冻剂、BHT等抗氧化剂、紫外线吸收剂等其它辅助剂。
有效成分化合物的配合比例可以根据需要增减,在本发明的农园艺用杀菌剂100重量份中,从0.01~90重量份的范围中适当选择使用即可,例如,在制成粉剂、粒剂、乳剂或可湿性粉剂的情况下,0.01~50重量份(除草剂整体的重量为0.01~50重量%)较为合适。
作为本发明的通式(I)表示的化合物或其盐类的使用量,考虑到例如目的、对象杂草,作物的生长发育状况、产生杂草的倾向、天气气候、环境条件、剂型、施药方法、施药场所、施药时段等各种因素,作为有效成分化合物,根据目的从每10公亩0.001g~10kg、优选地0.01g~1kg的范围中适当选择即可。
在使用包含本发明的通式(I)表示的化合物或其盐类作为活性成分的除草剂时,稀释为适当的浓度后散布或直接施药。
为了扩大待防治病害、防治适应期,或者为了降低药量,也可以将本发明的农园艺用杀菌剂与其它农园艺用杀虫剂、杀螨剂、杀线虫剂、杀菌剂、生物农药等混合后使用,另外,还可以根据使用场景与除草剂、植物生长调节剂、肥料等混合后使用。以下将示例代表性的化合物,但不限定于此。
作为为了上述目的而使用的其它农园艺用杀菌剂,例如,可示例:
金色制酶素(aureofungin)、氧环唑(azaconazole)、塞仑(azithiram)、阿普泰克(acypetacs)、活化酯(acibenzolar)、活化酯-S-甲基(acibenzolar-S-methyl)、嘧菌酯(azoxystrobin)、敌菌灵(anilazine)、吲唑磺菌胺(amisulbrom)、1-氨基丙基磷酸(ampropylfos)、辛唑嘧菌胺(ametoctradin)、烯丙醇(allylalcohol)、烯丙菊酯(aldimorph)、代森铵(amobam)、异噻菌胺(isotianil)、异酰菌酮(isovaledione)、吡唑萘菌胺(isopyrazam)、isofetamid、稻瘟灵(isoprothiolane)、种菌唑(ipconazole)、异菌脲(iprodione)、缬霉威(iprovalicarb)、异稻瘟净(iprobenfos)、抑霉唑(imazalil)、双胍辛胺(iminoctadine)、烷苯磺酸盐(iminoctadine-albesilate)、双胍辛胺三乙酸盐(iminoctadine-triacetate)、亚胺唑(imibenconazole)、烯效唑(uniconazole)、精烯效唑(uniconazole-P)、氯唑灵(echlomezole)、敌瘟磷(edifenphos)、乙环唑(etaconazole)、噻唑菌胺(ethaboxam)、乙嘧酚(ethirimol)、代森硫(etem)、乙氧喹啉(ethoxyquin)、土菌灵(etridiazole)、烯肟菌酯(enestroburin)、烯肟菌酯(enoxastrobin)、enoxastrobin、氟环唑(epoxiconazole)、噁霜灵(oxadixyl)、氟噻唑吡乙酮(oxathiapiprolin)、氟噻唑吡乙酮(oxathiapiprolin)、氧化萎锈灵(oxycarboxin)、8-羟基喹啉铜(copper-8-quinolinolate)、土霉素(oxytetracycline)、copper-oxinate、噁咪唑(oxpoconazole)、噁咪唑富马酸盐(oxpoconazole-fumarate)、喹菌酮(oxolinic acid)、辛噻酮(octhilinone)、呋酰胺(ofurace)、肟醚菌胺(orysastrobin)、威百亩-钠(metam-sodium)等土壤杀菌剂、
春雷霉素(kasugamycin)、吗菌威(carbamorph)、环丙酰菌胺(carpropamid)、多菌灵(carbendazim)、萎锈灵(carboxin)、香芹酮(carvone)、醌菌腙(quinazamid)、喹烯酮(quinacetol)、喹氧灵(quinoxyfen)、灭螨猛(chinomethionat)、灭螨锰(quinomethionate)、敌菌丹(captafol)、克菌丹(captan)、精苯霜灵(kiralaxyl)、氯苯喹唑(quinconazole)、五氯硝基苯(quintozene)、双胍辛胺(guazatine)、呋菌清(cufraneb)、杀菌威(cuprobam)、丁香菌酯(coumoxystrobin)、果绿啶(glyodin)、灰黄霉素(griseofulvin)、咪菌酮(climbazole)、甲酚(cresol)、苯氧菌酯(kresoxim-methyl)、乙菌利(chlozolinate)、克霉唑(clotrimazole)、灭瘟唑(chlobenthiazone)、双胺灵(chloraniformethan)、四氯对醌(chloranil)、四氯喹噁啉(chlorquinox)、氯化苦(chloropicrin)、氯苯咪唑(chlorfenazole)、氯硝萘(chlorodinitronaphthalene)、百菌清(chlorothalonil)、氯苯甲醚(chloroneb)、水杨酰苯胺(salicylanilide)、氰菌胺(zarilamid)、氰霜唑((cyazofamid)、焦碳酸二乙酯(diethyl pyrocarbonate)、乙霉威(diethofencarb)、环菌胺(cyclafuramid)、双氯氰菌胺(diclocymet)、菌核利(dichlozoline)、苄氯三唑醇(diclobutrazol)、苯氟磺胺(dichlofluanid)、放线菌酮(cycloheximide)、哒菌清(diclomezine)、氯硝胺(dicloran)、双氯酚(dichlorophen)、二氯萘醌(dichlone)、双硫仑(disulfiram)、灭菌磷(ditalimfos)、二氰蒽醌(dithianon)、烯唑醇(diniconazole)、R-烯唑醇(diniconazole-M)、代森锌(zineb)、敌螨普(dinocap)、敌螨通(dinocton)、硝辛酯(dinosulfon)、硝丁酯(dinoterbon)、消螨通(dinobuton)、硝戊酯(dinopenton)、dipymetitrone、dipymetitrone、双硫氧吡啶(dipyrithione)、二苯胺(diphenylamine)、苯醚甲环唑(difenoconazole)、环氟菌胺(cyflufenamid)、氟嘧菌胺(diflumetorim)、环丙唑醇(cyproconazole)、嘧菌环胺(cyprodinil)、酯菌胺(cyprofuram)、氰菌灵(cypendazole)、硅氟唑(simeconazole)、二甲嘧酚(dimethirimol)、烯酰吗啉(dimethomorph)、霜脲氰(cymoxanil)、醚菌胺(dimoxystrobin)、福美锌(ziram)、硅噻菌胺(silthiofam)、链霉素(streptomycin)、螺噁茂胺(spiroxamine)、戊苯砜(sultropen)、环丙吡菌胺(sedaxane)、苯酰菌胺(zoxamide)、棉隆(dazomet)、代森环(thiadiazin)、噻酰菌胺(tiadinil)、氟噻亚菌胺(thiadifluor)、噻菌灵(thiabendazole)、硫氰苯甲酰胺(tioxymid)、硫氯苯亚胺(thiochlorfenphim)、硫菌灵(thiophanate)、甲基硫菌灵(thiophanate-methyl)、噻呋酰胺(thifluzamide)、噻菌腈(thicyofen)、克杀螨(thioquinox)、福美双(thiram)、癸磷锡(decafentin)、四氯硝基苯(tecnazene)、叶枯酞(tecloftalam)、福美双联(tecoram)、四氟醚唑(tetraconazole)、咪菌威(debacarb)、脱氢乙酸(dehydroacetic acid)、戊唑醇(tebuconazole)、异丁乙氧喹啉(tebufloquin)、多地辛(dodicin)、多果定(dodine)、十二烷基苯磺酸双乙二胺铜络合物盐(II)(DBEDC)、十二环吗啉(dodemorph)、肼菌酮(drazoxolon)、三唑醇(triadimenol)、三唑酮(triadimefon)、丁基三唑(triazbutil)、咪唑嗪(triazoxide)、威菌磷(triamiphos)、嘧菌醇(triarimol)、水杨菌胺(trichlamide)、氯啶菌酯(triclopyricarb)、三环唑(tricyclazole)、灭菌唑(triticonazole)、石蜡油(tridemorph)、三丁基氧化锡(tributyltin oxide)、氟菌唑(triflumizole)、肟菌酯(trifloxystrobin)、嗪氨灵(triforine)、甲苯氟磺胺(tolylfluanid)、甲基立枯磷(tolclofos-methyl)、tolprocarb、那他霉素(natamycin)、代森钠(nabam)、硫氰散(nitrostyrene)、酞菌酯(nitrothal-isopropyl)、氟苯嘧啶醇(nuarimol)、壬菌铜(copper nonylphenol sulfonate)、丙烯酸喹啉酯(halacrinate)、有效霉素(validamycin)、缬菌胺(valifenalate)、超敏蛋白(harpinprotein)、picarbutrazox、联苯吡菌胺(bixafen)、啶氧菌酯(picoxystrobin)、picobenzamide、硫氯酚(bithionol)、联苯三唑醇(bitertanol)、土菌消(hydroxyisoxazole)、氢异噁唑钾(hydroisoxazole-potassium)、乐杀螨(binapacryl)、联苯(biphenyl)、哌丙灵(piperalin)、噁霉灵(hymexazol)、唑菌酯(pyraoxystrobin)、吡喃灵(pyracarbolid)、吡唑醚菌酯(pyraclostrobin)、pyraziflumid、吡菌磷(pyrazophos)、唑胺菌酯(pyrametostrobin)、甲氧苯啶菌(pyriofenone)、啶菌腈(pyridinitril)、氟唑菌酰羟胺(pydiflumetofen)、氟唑菌酰羟胺(pydiflumetofen)、啶菌噁唑(pyrisoxazole)、啶斑肟(pyrifenox)、吡菌苯威(pyribencarb)、嘧霉胺(pyrimethanil)、氯甲氧吡啶(pyroxychlor)、氯吡呋醚(pyroxyfur)、咯喹酮(pyroquilon)、乙烯菌核利(vinclozolin)、噁唑菌酮(famoxadone)、咪菌腈(fenapanil)、咪唑菌酮(fenamidone)、敌磺钠(fenaminosulf)、烯肟菌胺(fenaminstrobin)、氯苯嘧啶醇(fenarimol)、种衣酯(fenitropan)、稻瘟酰胺(fenoxanil)、嘧菌腙(ferimzone)、福美铁(ferbam)、三苯锡(fentin)、拌种咯(fenpiclonil)、胺苯吡菌酮(fenpyrazamine)、腈苯唑(fenbuconazole)、甲呋酰胺(fenfuram)、苯锈啶(fenpropidin)、丁苯吗啉(fenpropimorph)、环酰菌胺(fenhexamid)、苯酞(phthalide)、丁硫啶(buthiobate)、丁胺(butylamine)、乙嘧酚磺酸酯(bupirimate)、麦穗宁(fuberidazole)、灰瘟素(blasticidin-S)、福拉比(furametpyr)、呋霜灵(furalaxyl)、嘧螨酯(fluacrypyrim)、氟啶胺(fluazinam)、氟嘧菌酯(fluoxastrobin)、三氟苯唑(fluotrimazole)、氟吡菌胺(fluopicolide)、氟吡菌酰胺(fluopyram)、氟酰亚胺(fluoroimide)、二甲呋酰胺(furcarbanil)、氟苯吡菌胺(fluxapyroxad)、氟喹唑(fluquinconazole)、呋菌唑(furconazole)、呋醚唑(furconazole-cis)、咯菌腈(fludioxonil)、氟硅唑(flusilazole)、磺菌胺(flusulfamide)、磺菌胺(flutianil)、氟酰胺(flutolanil)、粉唑醇(flutriafol)、糠醛(furfural)、拌种胺(furmecyclox)、氟酰菌胺(flumetover)、氟吗啡(flumorph)、丙氧喹啉(proquinazid)、咪鲜胺(prochloraz)、腐霉利(procymidone)、硫菌威(prothiocarb)、丙硫菌唑(prothioconazole)、霜霉威(propamocarb)、丙环唑(propiconazole)、丙森锌(propineb)、呋甲硫菌灵(furophanate)、烯丙苯噻唑(probenazole)、糠菌唑(bromuconazole)、六氯丁二烯(hexachlorobutadiene)、己唑醇(hexaconazole)、hexylthiofos、bethoxazin、苯霜灵(benalaxyl)、苯霜灵-M(benalaxyl-M)、麦锈灵(benodanil)、苯菌灵(benomyl)、稻瘟酯(pefurazoate)、醌肟腙(benquinox)、戊菌唑(penconazole)、抑菌啉(benzamorf)、戊菌隆(pencycuron)、苯基异羟肟酸(benzohydroxamic acid)、苯并烯氟菌唑(benzovindiflupyr)、苯他隆(bentaluron)、苯噻硫氰(benthiazole)、苯噻菌胺-异丙基(benthiavalicarb-isopropyl)、吡噻菌胺(penthiopyrad)、戊苯吡菌胺(penflufen)、啶酰菌胺(boscalid)、氯瘟磷(phosdiphen)、三乙膦酸(fosetyl)、三乙膦酸铝(fosetyl-Al)、多抗霉素(polyoxins)、保粒霉素(polyoxorim)、代森福美锌(polycarbamate)、灭菌丹(folpet)、甲醛(formaldehyde)、机械油(machine oil)、代森锰(maneb)、代森锰锌(mancozeb)、双炔酰菌胺(mandipropamid)、mandestrobin、甲菌利(myclozolin)、腈菌唑(myclobutanil)、米多霉素(mildiomycin)、代森环(milneb)、苯并威(mecarbinzid)、磺菌威(methasulfocarb)、间氯敌菌酮(metazoxolon)、威百亩(metam)、威百亩(metam-sodium)、甲霜灵(metalaxyl)、精甲霜灵(metalaxyl-M)、代森联(metiram)、异硫氰酸甲酯(methylisothiocyanate)、敌螨普(mepthyldinocap)、叶菌唑(metconazole)、噻菌胺(metsulfovax)、呋菌胺(methfuroxam)、苯氧菌胺(metominostrobin)、苯菌酮(metrafenone)、嘧菌胺(mepanipyrim)、精甲霜灵(mefenoxam)、二硝巴豆酸酯(meptyldinocap)、灭锈胺(mepronil)、邻酰胺(mebenil)、碘甲烷(iodomethane)、吡咪唑(rabenzazole)、溴甲烷(methyl bromide)、苯扎氯铵(benzalkoniumchloride)、王铜(basic copper chloride)、碱式硫酸铜(basic coppersulfate)、金属银(silver)等无机杀菌剂、
次氯酸钠(sodium hypochlorote)、氢氧化铜(cupric hydroxide)、水合硫剂(wettable sulfur)、石硫合剂(calcium polysulfide)、碳酸氢钾(potassium hydrogencarbonate)、碳酸氢钠(sodium hydrogen carbonate)、无机硫(sulfur)、无水硫酸铜(copper sulfate anhydride)、福美镍(nickel dimethyldithiocarbamate)、喹啉铜(oxine copper)等铜类化合物、硫酸锌(zinc sulfate)、以及五水硫酸铜(copper sulfatepentahydrate)等。
作为为了相同的目的而使用的农园艺杀虫剂、杀螨剂、杀线虫剂,例如,可示例:
3,5-二甲苯基甲基氨基甲酸酯(xylyl methylcarbamate)(XMC)、苏云金芽孢杆菌aizawai(Bacillus thuringiensis aizawai)、苏云金芽孢杆菌israelensis(Bacillusthuringiensis israelensis)、苏云金芽孢杆菌japonensis(Bacillus thuringiensisjaponensis)、苏云金芽孢杆菌kurstaki(Bacillus thuringiensis kurstaki)、或苏云金芽孢杆菌tenebrionis(Bacillus thuringiensis tenebrionis)、苏云金芽孢杆菌(Bacillus thuringiensis)生成的晶体蛋白质毒素、BPMC、Bt毒素类杀虫性化合物、CPCBS(杀螨酯(chlorfenson))、DCIP(二氯二异丙基酯)、D-D(1,3-二氯丙烯(Dichloropropene))、DDT、NAC、O-4-二甲基氨磺酰基苯基O、O-二乙基硫代磷酸酯(O-4-dimethylsulfamoylphenyl O、O-diethyl phosphorothioate)(DSP)、O-乙基O-4-硝基苯基苯基硫代磷酸酯(O-ethyl O-4-nitrophenyl phenylphosphonothioate)(EPN)、三丙基异氰脲酸酯(tripropylisocyanurate)(TPIC)、氟丙菊酯(acrinathrin)、印楝素(azadirachtin)、保棉磷(azinphos-methyl)、灭螨醌(acequinocyl)、啶虫脒(acetamiprid)、乙酰虫腈(acetoprole)、乙酰甲胺磷(acephate)、阿维菌素(abamectin)、afidopyropen、阿维菌素-B(avermectin-B)、磺胺螨酯(amidoflumet)、双甲脒(amitraz)、棉铃威(alanycarb)、涕灭威(aldicarb)、涕灭砜威(aldoxycarb)、艾氏剂(aldrin)、α-硫丹(alpha-endosulfan)、顺式氯氰菊酯(alpha-cypermethrin)、除害威(albendazole)、烯丙菊酯(allethrin)、氯唑磷(isazofos)、isamidofos、isoamidofos、噁唑磷(isoxathion)、异柳磷(isofenphos)、异丙威(isoprocarb:MIPC)、epsilon-metofluthrin、epsilon-momfluorothrin、齐墩螨素(ivermectin)、新烟碱类(imicyafos)、吡虫啉(imidac1oprid)、炔咪菊酯(imiprothrin)、茚虫威(indoxacarb)、S-氰戊菊酯(esfenvalerate)、乙硫苯威(ethiofencarb)、乙硫磷(ethion)、乙虫腈(ethiprole)、乙螨唑(etoxazole)、醚菊酯(ethofenprox)、灭线磷(ethoprophos)、乙嘧硫磷(etrimfos)、甲氨基阿维菌素(emamectin)、甲氨基阿维菌素苯甲酸盐(emamectin-benzoate)、硫丹(endosulfan)、右旋烯炔菊酯(empenthrin)、杀线威(oxamyl)、亚砜磷(oxydemeton-methyl)、异砜磷(oxydeprofos:ESP)、奥苯达唑(oxibendazole)、磺唑氨酯(oxfendazole)、油酸钾(Potassium oleate)、油酸钠(sodium oleate)、硫酰磷(cadusafos)、kappa-bifenthrin、杀螟丹(cartap)、胺甲萘(carbaryl)、丁硫克百威(carbosulfan)、carbofuryan、精高效氯氟氰菊酯(gamma-cyhalothrin)、灭杀威(xylylcarb)、喹硫磷(quinalphos)、烯虫炔酯(kinoprene)、灭螨猛(chinomethionat)、除线威(cloethocarb)、噻虫胺(clothianidin)、四螨嗪(clofentezine)、环虫酰胺(chromafenozide)、氯虫苯甲酰胺(chlorantraniliprole)、氯氧磷(chlorethoxyfos)、杀虫脒(chlordimeform)、氯丹(chlordane)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、溴虫清(chlorphenapyr)、杀螨酯(chlorfenson)、毒虫畏(ch1orfenvinphos)、氟啶脲(chlorfluazuron)、乙酯杀螨醇(chlorobenzilate)、氯代苯甲酸酯(chlorobenzoate)、氯丙炔菊酯(chloroprallethrin)、三氯杀螨醇(dicofol)、蔬果磷(salithion)、cyhalodiamide、杀螟腈(cyanophos:CYAP)、丁醚脲(diafenthiuron)、除线特(diamidafos)、氰虫酰胺(cyantraniliprole)、θ-氯氰菊酯(theta-cypermethrin)、除螨灵(dienochlor)、腈吡螨酯(cyenopyrafen)、蔬果磷(dioxabenzofos)、苯虫醚(diofenolan)、σ-氯氰菊酯(sigma-cypermethrin)、cyclaniliprole、除线磷(dichlofenthion:ECP)、乙氰菊酯(cycloprothrin)、敌敌畏(dichlorvos:DDVP)、乙拌磷(disulfoton)、呋虫胺(dinotefuran)、氯氟氰菊酯(cyhalothrin)、苯醚氰菊酯(cyphenothrin)、β-氟氯氰菊酯(cyfluthrin)、除虫脲(diflubenzuron)、丁氟螨酯(cyflumetofen)、氟螨嗪(diflovidazin)、三环锡(cyhexatin)、氯氰菊酯(cypermethrin)、甲基毒虫畏(dimethylvinphos)、乐果(dimethoate)、四氟甲醚菊酯(dimefluthrin)、灭虫硅醚(silafluofen)、灭蝇胺cyromazine)、乙基多杀菌素(spinetoram)、艾克敌(spinosad)、螺螨酯(spirodiclofen)、螺虫乙酯(spirotetramat)、螺甲螨酯(spiromesifen)、氟虫胺(sulfluramid)、硫丙磷(sulprofos)、氟啶虫胺腈(sulfoxaflor)、ζ-氯氰菊酯(zeta-cypermethrin)、二嗪磷(diazinon)、τ-氟胺氰菊酯(tau-fluvalinate)、棉隆(dazomet)、噻虫啉(thiacloprid)、噻虫嗪(thiamethoxam)、tioxazafen、硫双威(thiodicarb)、杀虫环(thiocyclam)、杀虫双(thiosultap)、杀虫双(thiosultap-sodium)、虫线磷(thionazin)、甲基乙拌磷(thiometon)、避蚊胺(deet)、狄氏剂(dieldrin)、杀虫威(tetrach1orvinphos)、三氯杀螨砜(tetradifon)、tetraniliprole、四氟醚菊酯(tetramethylfluthrin)、胺菊酯(tetramethrin)、嘧丙磷(tebupirimfos)、虫酰肼(tebufenozide)、吡螨胺(tebufenpyrad)、七氟菊酯(tefluthrin)、氟苯脲(teflubenzuron)、内吸磷-S-甲基(demeton-S-methyl)、双硫磷(temephos)、溴氰菊酯(deltamethrin)、特丁硫酸(terbufos)、溴代吡咯腈(tralopyril)、四溴菊酯(tralomethrin)、四氟苯菊酯(transfluthrin)、唑蚜威(triazamate)、唑呀威(triazuron)、水杨菌胺(trichlamide)、敌百虫(trichlorphon:DEP)、三氟苯嘧啶(triflumezopyrim)、杀铃脲(triflumuron)、唑虫酰胺(tolfenpyrad)、ナレッド(naled:BRP)、噻虫醛(nithiazine)、烯啶虫胺(nitenpyram)、氟酰脲(novaluron)、多氟脲(noviflumuron)、烯虫乙酯(hydroprene)、氟吡唑虫(vaniliprole)、蚜灭多(vamidothion)、对硫磷(parathion)、甲基对硫磷(parathion-methyl)、苄螨醚(halfenprox)、特丁苯酰肼(halofenozide)、双三氟虫脲(bistrifluron)、杀虫双(bisultap)、氟蚁腙(hydramethylnon)、羟丙基淀粉(hydroxy propyl starch)、乐杀螨(binapacryl)、pyflubumide、联苯肼酯(bifenazate)、联苯菊酯(bifenthrin)、吡蚜酮(pymetrozine)、吡唑硫磷(pyraclofos)、嘧啶威(pyrafluprole)、哒嗪硫磷(pyridafenthion)、哒螨灵(pyridaben)、啶虫丙醚(pyridalyl)、氟虫吡喹(pyrifluquinazon)、吡啶醇(pyriprole)、吡丙醚(pyriproxyfen)、抗蚜威(pirimicarb)、嘧螨醚(pyrimidifen)、pyriminostrobin、甲基嘧啶磷(pirimiphos-methyl)、除虫菊酯(pyrethrins)、氟虫腈(fiproni1)、喹螨醚(fenazaquin)、苯线磷(fenamiphos)、溴螨酯(bromopropylate)、杀螟松(fenitrothion:MEP)、双氧威(fenoxycarb)、苯硫威(fenothiocarb)、苯醚菊酯(phenothrin)、仲丁威(fenobucarb)、丰索磷(fensulfothion)、倍硫磷(fenthion:MPP)、稻丰散(phenthoate:PAP)、氰戊菊酯(fenvalerate)、唑螨酯(fenpyroximate)、甲氰菊酯(fenpropathrin)、芬苯达唑(fenbendazole)、噻唑膦(fosthiazate)、伐虫脒(formetanate)、特嘧硫磷(butathiofos)、噻嗪酮(buprofezin)、呋线威(furathiocarb)、右旋炔丙菊酯(prallethrin)、嘧螨酯(fluacrypyrim)、fluazaindolizine、氟啶胺(fluazinam)、啶蜱脲(fluazuron)、氟烯线砜(fluensulfone)、fluxametamide、氟螨脲(flucycloxuron)、氟氰戊菊酯(flucythrinate)、氟胺氰菊酯(fluvalinate)、丁虫腈(flufiprole)、氟吡呋喃酮(flupyradifurone)、吡氟硫磷(flupyrazofos)、嘧虫胺(flufenerim)、flufenoxystrobin、氟虫脲(flufenoxuron)、氟螨嗪(flufenzine)、氟丙苄醚(flufenprox)、苄螨醚(fluproxyfen)、溴氟菊酯(flubrocythrinate)、fluhexafon、氟苯虫酰胺(flubendiamide)、氟氯苯菊酯(flumethrin)、flurimfen、丙硫磷(prothiofos)、丙苯烃菊酯(protrifenbute)、氟啶虫酰胺(flonicamid)、丙虫磷(propaphos)、炔螨特(propargite:BPPS)、丙溴磷(profenofos)、丙氟菊酯(profluthrin)、残杀威(propoxur:PHC)、flometoquin、溴螨酯(bromopropylate)、β-氟氯氰菊酯(beta-cyfluthrin)、氟铃脲(hexaflumuron)、噻螨酮(hexythiazox)、heptafluthrin、庚虫磷(heptenophos)、氯菊酯(permethrin)、7-氯-1,2-苯并异噻唑(benclothiaz)、噁虫威(bendiocarb)、杀虫磺(bensultap)、苯螨特(benzoximate)、丙硫克百威(benfuracarb)、辛硫磷(phoxim)、伏杀硫磷(phosalone)、噻唑膦(fosthiazate)、丁硫环磷(fosthietan)、磷胺(phosphamidon)、乙丙磷威(phosphocarb)、亚胺硫磷(phosmet:PMP)、抗螨素复合体(polynactins)、伐虫脒(formetanate)、安硫磷(formothion)、甲拌磷(phorate)、机械油(machine oil)、马拉硫磷(malathion)、米尔倍霉素(milbemycin)、米尔倍霉素A(milbemycin-A)、米尔螨素(milbemectin)、灭蚜磷(mecarbam)、甲亚砜磷(mesulfenfos)、灭多威(methomyl)、四聚乙醛(metaldehyde)、氰氟虫腙(metaflumizone)、甲胺磷(methamidophos)、威百亩-铵(metam-ammonium)、威百亩-钠(metam-sodium)、甲硫威(methiocarb)、杀扑磷(methidathion:DMTP)、异硫氰酸甲酯(methylisothiocyanate)、甲基新癸酰胺(methylneodecanamide)、甲基对硫磷(methylparathion)、噁虫酮(metoxadiazone)、甲氧氯(methoxychlor)、甲氧虫酰肼(methoxyfenozide)、甲氧苄氟菊酯(metofluthrin)、烯虫酯(methoprene)、速灭威(metolcarb)、氯氟醚菊酯(meperfluthrin)、速灭磷(mevinphos)、久效磷(monocrotophos)、杀虫丹(monosultap)、momfluorothrin、高效氯氟氰菊酯(lambda-cyhalothrin)、兰尼碱(ryanodine)、虱螨脲(lufenuron)、rescalure、苄呋菊酯(resmethrin)、雷皮菌素(lepimectin)、鱼藤酮(rotenone)、盐酸左旋咪唑(levamisolhydrochloride)、苯丁锡(fenbutatin oxide)、酒石酸甲噻嘧啶(morantel tartarate)、溴甲烷(methyl bromide)、三环锡(cyhexatin)、氰氨化钙(calcium cyanamide)、石硫合剂(calcium polysulfide)、硫(sulfur)、及硫酸化烟碱(nicotine-sulfate)等。
作为为了相同的目的而使用的除草剂,例如,可示例:1-萘基乙酰胺(1-naphthylacetamide)、2,4-PA、2,3,6-TBA、2,4,5-T、2,4,5-TB、2,4-D、2,4-DB、2,4-DEB、2,4-DEP、3,4-DA、3,4-DB、3,4-DP、4-CPA、4-CPB、4-CPP、MCP、MCPA、2甲4氯乙硫酯(MCPA-thioethyl)、MCPB、碘苯腈(ioxynil)、苯草醚(aclonifen)、唑啶炔草(azafenidin)、三氟羧草醚(acifluorfen)、叠氮净(aziprotryne)、四唑嘧磺隆(azimsulfuron)、磺草灵(asulam)、乙草胺(acetochlor)、莠去津(atrazine)、阿特拉通(atraton)、疏草隆(anisuron)、莎椑磷(anilofos)、艾维激素(aviglycine)、诱抗素(abscisic acid)、氨唑草酮(amicarbazone)、酰嘧磺隆(amidosulfuron)、杀草强(amitrole)、环丙嘧啶酸(aminocyclopyrachlor)、氯氨基吡啶酸(aminopyralid)、特草嗪酮(amibuzin)、甲基胺草磷(amiprophos-methyl)、特津酮(ametridione)、莠灭净(ametryn)、甲草胺(alachlor)、二丙烯草胺(allidochlor)、禾草灭(alloxydim)、五氯戊酮酸(alorac)、依马刹媒刹哌(iofensulfuron)、异噁隆(isouron)、丁咪酰胺(isocarbamid)、异噁氯草酮(isoxachlortole)、异噁草醚(isoxapyrifop)、异噁氟草酮(isoxaflutole)、异噁酰草胺(isoxaben)、异草定(isocil)、异草完隆(isonoruron)、异丙隆(isoproturon)、异丙乐灵(isopropalin)、氮草(isopolinate)、丁嗪草酮(isomethiozin)、抗倒胺(inabenfide)、抑草津(ipazine)、卤苯胺唑(ipfencarbazone)、丙草定(iprymidam)、咪唑喹啉酸(imazaquin)、甲咪唑烟酸(imazapic)、咪唑烟酸(imazapyr)、imazamethapyr、咪草酯(imazamethabenz)、咪草酯-甲基(imazamethabenz-methyl)、甲氧咪草烟(imazamox)、咪唑乙烟酸(imazethapyr)、唑吡嘧磺隆(imazosulfuron)、茚嗪氟草胺(indaziflam)、茚草酮(indanofan)、吲哚丁酸(indolebutyric acid)、精烯效唑(uniconazole-P)、甘草津(eglinazine)、戊草丹(esprocarb)、胺苯磺隆脱甲基酸(ethametsulfuron)、胺苯磺隆(ethametsulfuron-methyl)、乙丁烯氟灵(ethalfluralin)、硫草敌(ethiolate)、ethychlozate ethyl、磺噻隆(ethidimuron)、硝草酚(etinofen)、乙烯利(ethephon)、乙氧嘧磺隆(ethoxysulfuron)、氯氟草醚(ethoxyfen)、乙胺草醚(etnipromid)、乙呋草磺(ethofumesate)、乙氧苯草胺(etobenzanid)、磺唑草(epronaz)、抑草蓬(erbon)、茵多酸(endothal)、噁草酮(oxadiazon)、丙炔噁草酮(oxadiargyl)、氯噁嗪草(oxaziclomefone)、环氧嘧磺隆(oxasulfuron)、噁杀草敏(oxapyrazon)、乙氧呋草醚(oxyfluorfen)、氨磺乐灵(oryzalin)、嘧苯胺磺隆(orthosulfamuron)、坪草丹(orbencarb)、唑草胺(cafenstrole)、克草胺酯(cambendichlor)、卡巴草灵(carbasulam)、唑草酮(carfentrazone)、唑酮草酯(carfentrazone-ethyl)、特胺灵(karbutilate)、双酰草胺(carbetamide)、特噁唑威(carboxazole)、喹禾灵(quizalofop)、精喹禾灵(quizalofop-P)、喹禾灵-乙基(quizalofop-ethyl)、二甲苯草胺(xylachlor)、灭藻醌(quinoclamine)、氯藻胺(quinonamid)、二氯喹啉酸(quinclorac)、氯甲喹啉酸(quinmerac)、苄草隆(cumyluron)、碘氯啶酯(cliodinate)、草甘膦(glyphosate)、草铵膦(glufosinate)、精草铵膦(glufosinate-P)、醚草敏(credazine)、烯草酮(clethodim)、座果酸(cloxyfonac)、炔草酯(clodinafop)、炔草酯-炔丙基(clodinafop-propargyl)、氯麦隆(chlorotoluron)、二氯吡啶酸(clopyralid)、环丁烯草酮(cloproxydim)、调果酸(cloprop)、氯溴隆(chlorbromuron)、氯丁草(clofop)、异噁草酮(clomazone)、氯硝醚(chlomethoxyni1)、甲氧除草醚(chlomethoxyfen)、稗草胺(clomeprop)、炔禾灵(chlorazifop)、可乐津(chlorazine)、氯酯磺草胺(cloransulam)、丁酰草胺(chloranocryl)、草灭畏(chloramben)、氯酯磺草胺(cloransulam-methyl)、氯草敏(chloridazon)、氯嘧磺隆脱乙基酸(chlorimuron)、氯嘧磺隆(chlorimuron-ethyl)、氯磺隆(chlorsulfuron)、氯酞酸(chlorthal)、氯硫酰草胺(chlorthiamid)、绿麦隆(chlortoluron)、草枯醚(chlornitrofen)、伐草克(chlorfenac)、燕麦酯(chlorfenprop)、氯炔灵(chlorbufam)、氟嘧杀(chlorflurazole)、整形醇(chlorflurenol)、草败死(chlorprocarb)、氯苯胺灵(chlorpropham)、矮壮素(chlormequat)、乙氧苯隆(chloreturon)、羟敌草腈(chloroxynil)、枯草隆(chloroxuron)、三氯丙酸(chloropon)、苯嘧磺草胺(saflufenacil)、氰草津(cyanazine)、氰草净(cyanatryn)、燕麦敌(di-allate)、敌草隆(diuron)、二乙除草双(diethamquat)、麦草畏(dicamba)、环莠隆(cycluron)、环草敌(cycloate)、噻草酮(cycloxydim)、唑嘧磺胺(diclosulam)、环丙嘧磺隆(cyclosulfamuron)、cyclopyrimorate、2,4-滴丙酸(dichlorprop)、精2,4-滴丙酸(dichlorprop-P)、敌草腈(dichlobenil)、禾草灵(diclofop)、禾草灵-甲基(diclofop-methyl)、苄胺灵(dichlormate)、氯全隆(dichloralurea)、敌草快(diquat)、咯草隆(cisanilide)、2,4-滴硫钠(disul)、环草隆(siduron)、氟硫草定(dithiopyr)、氨氟灵(dinitramine)、吲哚酮草酯(cinidon-ethyl)、戊硝酚(dinosam)、醚磺隆(cinosulfuron)、地乐酚(dinoseb)、特乐酚(dinoterb)、地乐特(dinofenate)、丙硝酚(dinoprop)、氰氟草酯-丁基(cyhalofop-butyl)、双苯酰草胺(diphenamid)、枯莠隆(difenoxuron)、氟苯戊烯酸(difenopenten)、野燕枯(difenzoquat)、cybutryne、环丙津(cyprazine)、三环塞草胺(cyprazole)、吡氟酰草胺(diflufenican)、二氟吡隆(diflufenzopyr)、异丙净(dipropetryn)、环酰草胺(cypromid)、牧草快(cyperquat)、赤霉素(gibberellin)、西玛津(simazine)、敌灭生(dimexano)、二甲草胺(dimethachlor)、敌米达松(dimidazon)、戊草津(dimethametryn)、二甲吩草胺(dimethenamid)、西草净(simetryn)、西玛通(simeton)、哌草丹(dimepiperate)、噁唑隆(dimefuron)、环庚草醚(cinmethylin)、灭草灵(swep)、吖庚磺酯(sulglycapin)、磺草酮(sulcotrione)、菜草畏(sulfallate)、甲磺草胺(sulfentrazone)、磺酰磺隆(sulfosulfuron)、甲嘧磺隆脱甲基酸(sulfometuron)、甲嘧磺隆(sulfometuron-methyl)、密草通(secbumeton)、烯禾啶(sethoxydim)、另丁津(sebuthylazine)、特草定(terbacil)、香草隆(daimuron)、棉隆(dazomet)、茅草枯(dalapon)、赛唑隆(thiazafluron)、噻唑烟酸(thiazopyr)、汰芬那(tiafenacil)、thiencarbazone、噻酮磺隆(thiencarbazone-methyl)、仲草丹(tiocarbazil)、嘧草胺(tioclorim)、甲硫苯威(thiobencarb)、噻二唑胺(thidiazimin)、噻苯隆(thidiazuron)、噻吩磺隆脱甲基酸(thifensulfuron)、噻吩磺隆(thifensulfuron-methyl)、甜菜安(desmedipham)、敌草净(desmetryn)、四氟隆(tetrafluron)、噻吩草胺(thenylchlor)、牧草胺(tebutam)、丁噻隆(tebuthiuron)、甲氧去草净(terbumeton)、吡喃草酮(tepraloxydim)、特呋三酮(tefuryltrione)、环磺酮(tembotrione)、异丁草胺(delachlor)、特草定(terbacil)、特草灵(terbucarb)、特丁草胺(terbuchlor)、特丁津(terbuthylazine)、特丁净(terbutryn)、苯唑草酮(topramezone)、三甲苯草酮(tralkoxydim)、三嗪氟草胺(triaziflam)、醚苯磺隆(triasulfuron)、氟酮磺草胺(triafamone)、野麦畏(tri-allate)、草达津(trietazine)、杀草畏(tricamba)、绿草定(triclopyr)、灭草环(tridiphane)、草达克(tritac)、三氟甲磺隆(tritosulfuron)、trifludimoxazin、氟胺磺隆脱甲基酸(triflusulfuron)、氟胺磺隆(triflusulfuron-methyl)、氟乐灵(trifluralin)、三氟啶磺隆(trifloxysulfuron)、茚草酮(tripropindan)、苯磺隆(tribenuron-methyl)、苯磺隆脱甲基酸(tribenuron)、三氟苯氧丙酸(trifop)、三氟禾草肟(trifopsime)、三甲隆(trimeturon)、tolpyralate、萘草胺(naptalam)、萘丙胺(naproanilide)、敌草胺(napropamide)、烟嘧磺隆(nicosulfuron)、甲磺乐灵(nitralin)、除草醚(nitrofen)、三氟甲草醚(nitrofluorfen)、吡氯草胺(nipyraclofen)、草不隆(neburon)、氟草敏(norflurazon)、草完隆(noruron)、燕麦灵(barban)、多效唑(paclobutrazol)、百草枯(paraquat)、对伏隆(parafluron)、卤草定(haloxydine)、氟氯吡啶酯(游离酸)(halauxifen)、氟吡禾灵(haloxyfop)、高效氟吡甲禾灵(haloxyfop-P)、氟吡甲禾灵(haloxyfop-methyl)、氟硝磺酰胺(halosafen)、氯吡嘧磺隆脱甲基酸(halosulfuron)、氯吡嘧磺隆(halosulfuron-methyl)、氨氯吡啶酸(picloram)、氟吡酰草胺(picolinafen)、二环吡草酮(bicyclopyrone)、双草醚(bispyribac)、双草醚-钠(bispyribac-sodium)、比达农(pydanon)、唑啉草酯(pinoxaden)、甲羧除草醚(bifenox)、哌草磷(piperophos)、噁霉灵(hymexazol)、双唑草腈(pyraclonil)、磺酰草吡唑(pyrasulfotole)、苄草唑(pyrazoxyfen)、吡嘧磺隆脱乙基酸(pyrazosulfuron)、吡嘧磺隆(pyrazosulfuron-ethyl)、吡唑特(pyrazolate)、双丙氨酰膦(bilanafos)、吡草醚-乙基(pyraflufen-ethyl)、氯草定(pyriclor)、3-苯基-4-羟基-6-氯哒嗪(pyridafol)、嘧草硫醚(pyrithiobac)、嘧草硫醚-钠(pyrithiobac-sodium)、哒草特(pyr idate)、环酯草醚(pyriftalid)、稗草丹(pyributicarb)、嘧啶肟草醚(pyribenzoxim)、嘧氟磺草胺(pyrimisulfan)、氟嘧磺隆脱甲基酸(primisulfuron)、嘧草醚-甲基(pyriminobac-methyl)、砜吡草唑(pyroxasulfone)、啶磺草胺(pyroxsulam)、酰苯磺威(fenasulam)、棉胺宁(phenisopham)、非草隆(fenuron)、异噁苯砜(fenoxasulfone)、噁唑禾草灵(fenoxaprop)、精噁唑禾草灵(fenoxaprop-P)、噁唑禾草灵-乙基(fenoxaprop-ethyl)、酚硫杀(phenothio1)、2,4,5-涕丙酸(fenoprop)、酰草隆(phenobenzuron)、fenquinotrione、噻唑禾草灵(fenthiaprop)、氯苯氧乙醇(fenteracol)、四唑草胺(fentrazamide)、甜菜宁(phenmedipham)、甜菜宁-乙基(phenmedipham-ethyl)、丁草胺(butachlor)、氟丙嘧草酯(butafenacil)、抑草磷(butamifos)、丁噻隆(buthiuron)、特咪唑草(buthidazole)、丁草特(butylate)、炔草隆(buturon)、丁烯草胺(butenachlor)、丁苯草酮(butroxydim)、仲丁灵(butralin)、啶嘧磺隆(flazasulfuron)、麦草氟(flamprop)、呋氧草醚(furyloxyfen)、丙炔草胺(prynachlor)、氟嘧磺隆(primisulfuron-methyl)、吡氟禾草灵(fluazifop)、精吡氟禾草灵(fluazifop-P)、吡氟禾草灵-丁基(fluazifop-butyl)、异丙吡草酯(fluazolate)、氯氟吡氧乙酸(fluroxypyr)、氟苯隆(fluothiuron)、氟草隆(fluometuron)、乙羧氟草醚(fluoroglycofen)、氟咯草酮(flurochloridone)、三氟硝草醚(fluorodifen)、氟除草醚(fluoronitrofen)、唑啶草(fluoromidine)、氟酮磺隆(flucarbazone)、氟酮磺隆-钠(flucarbazone-sodium)、氯乙氟灵(fluchloralin)、氟吡磺隆(flucetosulfuron)、达草氟(fluthiacet)、达草氟-甲基(fluthiacet-methyl)、氟啶嘧磺隆脱甲基酸(flupyrsulfuron)、氟噻草胺(flufenacet)、氟苯吡草(flufenican)、氟哒嗪草酯(flufenpyr)、flupropacil、四氟丙酸(flupropanate)、氟胺草唑(flupoxam)、丙炔氟草胺(flumioxazin)、氟烯草酸(flumiclorac)、氟烯草酸-戊基(flumiclorac-pentyl)、炔草胺(flumipropyn)、三氟噁嗪(flumezin)、氟草隆(fluometuron)、唑嘧磺草胺(flumetsulam)、氟啶草酮(fluridone)、呋草酮(flurtamone)、氯氟吡氧乙酸(fluroxypyr)、丙草胺(pretilachlor)、扑灭生(proxan)、甘扑津(proglinazine)、环氰津(procyazine)、氨氟乐灵(prodiamine)、唑啉草酯磺亚胺草(prosulfalin)、氟磺隆(prosulfuron)、苄草丹(prosulfocarb)、噁草酸(propaquizafop)、毒草胺(propachlor)、扑灭津(propazine)、敌稗(propanil)、炔苯酰草胺(propyzamide)、异丙草胺(propisochlor)、茉莉酮(prohydrojasmon)、嗪咪唑嘧磺隆(propyrisulfuron)、苯胺灵(propham)、氟唑草胺(profluazol)、环丙氟灵(profluralin)、调环酸-钙(prohexadione-calcium)、丙苯磺隆(propoxycarbazone)、丙苯磺隆-钠(propoxycarbazone-sodium)、环苯草酮(profoxydim)、除草定(bromacil)、溴莠敏(brompyrazon)、扑草净(prometryn)、扑灭通(prometon)、溴苯腈(bromoxynil)、溴酚肟(bromofenoxim)、溴丁酰草胺(bromobutide)、糠草腈(bromobonil)、双氟磷草胺(florasulam)、florpyrauxifen、六氯丙酮(hexachloroacetone)、环嗪酮(hexazinone)、烯草胺(pethoxamid)、草除灵(benazolin)、五氟磺草胺(penoxsulam)、克草敌(pebulate)、氟丁酰草胺(beflubutamid)、灭草敌(vernolate)、氟草磺胺(perfluidone)、bencarbazone、胺酸杀(benzadox)、苄草胺(benzipram)、苄氨基嘌呤(benzylaminopurine)、苯噻隆(benzthiazuron)、双苯嘧草酮(benzfendizone)、地散磷(bensulide)、苄嘧磺隆(bensulfuron-methyl)、新燕灵(benzoylprop)、苯并双环酮(benzobicyclon)、吡草酮(benzofenap)、氟磺胺草(benzofluor)、灭草松(bentazone)、甲氯酰草胺(pentanochlor)、禾草丹(benthiocarb)、二甲戊灵(pendimethalin)、戊噁唑草(pentoxazone)、乙丁氟灵(benfluralin)、呋草黄(benfuresate)、杀木膦(fosamine)、氟磺胺草醚(fomesafen)、甲酰胺磺隆(foramsulfuron)、氯吡脲(forchlorfenuron)、马来酸酰肼(maleichydrazide)、2甲4氯丙酸(mecoprop)、精2甲4氯丙酸(mecoprop-P)、、丁硝酚(medinoterb)、甲磺胺磺隆脱甲基酸(mesosulfuron)、甲磺胺磺隆(mesosulfuron-methyl)、硝磺草酮(mesotrione)、灭莠津(mesoprazine)、盖草津(methoprotryne)、吡唑草胺(metazachlor)、灭草唑(methazole)、双醚氯吡嘧磺隆(metazosulfuron)、甲基苯噻隆(methabenzthiazuron)、苯嗪草酮(metamitron)、噁唑酰草胺(metamifop)、威百亩(metam)、氟烯硝草(methalpropalin)、灭草恒(methiuron)、噁噻草醚(methiozolin)、甲硫苯威(methiobencarb)、甲基杀草隆(methyldymron)、甲氧隆(metoxuron)、磺草唑胺(metosulam)、甲磺隆脱甲基酸(metsulfuron)、甲磺隆(metsulfuron-methyl)、氟哒草(metflurazon)、溴谷隆(metobromuron)、吡喃隆(metobenzuron)、醚草通(methometon)、异丙甲草胺(metolachlor)、嗪草酮(metribuzin)、缩节胺(mepiquat-chloride)、苯噻酰草胺(mefenacet)、氟磺酰草胺(mefluidide)、庚酰草胺(monalide)、特噁唑隆(monisouron)、灭草隆(monuron)、一氯乙酸(monochloroacetic acid)、绿谷隆(monolinuron)、禾草敌(molinate)、伐草快(morfamquat)、碘甲磺隆脱甲基酸(iodosulfuron)、碘甲磺隆-钠(iodosulfuron-methyl-sodium)、碘草腈(iodobonil)、碘甲烷(iodomethane)、乳氟禾草灵(lactofen)、利谷隆(linuron)、砜嘧磺隆(rimsulfuron)、环草定(lenacil)、硫氰苯乙胺(rhodethanil)、过氧化钙(calcium peroxide)、溴甲烷(methyl bromide)等。
另外,作为生物农药,例如,通过与核多角体病毒(Nuclear polyhedrosis virus、NPV)、颗粒病病毒(Granulosis virus、GV)、胞质多形体病毒(Cytoplasmic polyhedrosisvirus、CPV)、昆虫痘病毒(Entomopoxi virus、EPV)等病毒制剂、瘤捕单顶孢菌(Monacrosporiumphymatophagum)、斯氏线虫(Steinernemacarpocapsae)、昆虫寄生性线虫(Steinernemakushidai)、及穿刺芽孢杆(Pasteuriapenetrans)等用作杀虫或杀线虫剂的微生物农药;木素木霉(Trichoderma lignorum)、放射形土壤杆菌(Agrobacteriumradiobactor)、非病原性欧文氏杆菌(Erwinia carotovora)、及枯草芽孢杆菌(Bacillussubtilis)等用作杀菌剂的微生物农药;以及野油菜黄单胞菌(Xanthomonas campestris)等用作除草剂的生物农药等混合后使用,能够期待相同的效果。
而且,作为生物农药,例如,也可以与丽蚜小蜂(Encarsiaformosa)、科列马·阿布拉小蜂(Aphidiuscolemani)、食蚜瘿蚊(Aphidoletesaphidimyza)、イ豌豆潜蝇姬小蜂(Diglyphusisaea)、西伯利亚离颚茧蜂(Dacnusasibirica)、智利小植绥螨(Phytoseiuluspersimilis)、胡瓜钝绥螨(Amblyseiuscucumeris)、东亚小花蝽(Oriussauteri)等天敌生物;布氏白僵菌(Beauveria brongniartii)等微生物农药;以及(Z)-10-十四碳烯基=醋酸酯、(E,Z)-4,10-十四碳二烯基=醋酸酯、(Z)-8-十二碳烯基=醋酸酯、(Z)-11-十四碳烯基=醋酸酯、(Z)-13-二十碳-10-酮、14-甲基-1-十八碳烯等信息素剂并用。
以下将示例本发明的代表性实施例,但本发明不限定于此。
【实施例】
实施例1
N-(甲氧基{4-[5-(三氟甲基)-1,2,4-噁唑-3-基苯基]甲基})丁基酰胺(化合物编号1-13)的制造
【化学式6】
将通过国际公开第2017/055473号小册子中记载的方法制造的4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲醛(0.64g,2.7mmol)在氩气氛下溶解于氯仿(25mL),加入丁基酰胺(0.28g,3.2mmol)、甲醇钛(IV)(0.82g,4.8mmol),并在室温下搅拌17小时。然后,升温至45℃,搅拌5小时后,加入0.5M碳酸钾水溶液,搅拌15分钟。加入醋酸乙酯,通过硅藻土过滤除去所析出的固体,减压浓缩滤液。通过硅胶柱层析精制得到的残渣,从而得到标题化合物(0.25g,0.73mmol)。
收率:28%
物性值:熔点151-152℃
实施例2
N-(甲氧基{4-[5-(三氟甲基)-1,2,4-噁唑-3-基苯基]甲基})-N-甲基丁基酰胺(化合物编号1-19)的制造
【化学式7】
将N-{[4-(N’-羟基甲脒基(カルバモイミドイ))苯基]甲氧基甲基}-N-甲基丁基酰胺(0.27g,0.96mmol)溶解于氯仿(7mL),加入吡啶(0.37g,4.8mmol)、三氟醋酸酐(0.40g,1.9mmol),在室温下搅拌45分钟。然后,加入水,并用醋酸乙酯提取。将有机层用饱和食盐水清洗后,用硫酸钠干燥,并减压浓缩。通过硅胶柱层析精制得到的残渣,从而得到标题化合物(0.24g,0.68mmol)。
收率:71%
物性值:折射率(nD)1.3559(20.4℃)
实施例3
N-(甲氧基{2-(甲基硫基)-4-[5-(三氟甲基)-1,2,4-噁唑-3-基苯基]甲基})丁基酰胺(化合物编号1-132)的制造
【化学式8】
将2-(甲基硫基)-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲醛(0.48g,1.7mmol)在氩气氛下溶解于氯仿(12mL),加入丁基酰胺(0.17g,2.0mmol)、甲醇钛(IV)(0.51g,3.0mmol),并在室温下搅拌1.5小时。然后,升温至45℃,搅拌3.5小时后,在室温下静置16小时。然后,升温至45℃,搅拌3小时后,在室温下搅拌4小时。然后,升温至45℃,搅拌1小时后,在室温下静置17.5小时。然后,升温至45℃,搅拌2.5小时。然后,加入硅胶搅拌15分钟后,减压浓缩。通过硅胶柱层析精制得到的残渣,从而得到标题化合物(0.25g,0.64mmol)。
收率:39%
物性值:熔点154-155℃
实施例4
N-(甲氧基{2-(甲基磺酰基)-4-[5-(三氟甲基)-1,2,4-噁唑-3-基苯基]甲基})丁基酰胺(化合物编号1-134)及N-(甲氧基{2-(甲基亚磺酰基)-4-[5-(三氟甲基)-1,2,4-噁唑-3-基苯基]甲基})丁基酰胺(化合物编号1-135と化合物编号1-136)的制造
【化学式9】
(式中,n表示1~2的整数。)
将N-(甲氧基{2-(甲基硫基)-4-[5-(三氟甲基)-1,2,4-噁唑-3-基苯基]甲基})丁基酰胺(0.19g,0.48mmol)溶解于氯仿(5mL),冷却至0℃,加入间氯过苯甲酸(0.18g,0.72mmol),在室温下搅拌5.5小时。然后,加入饱和碳酸氢钠水溶液,并用醋酸乙酯提取。将有机层用饱和食盐水清洗后,用硫酸钠干燥,减压浓缩。通过硅胶柱层析精制得到的残渣,从而得到标题砜体(0.057g,0.14mmol)及两种亚砜体的非对映体(0.074g,0.18mmol(低极性非对映体)、0.064g,0.16mmol(高极性非对映体))。
收率:28%(砜体),38%(亚砜体、低极性非对映体),33%(亚砜体、高极性非对映体)
物性值:熔点158-159℃(砜体)、熔点148-149℃(亚砜体、低极性非对映体)、熔点177-179℃(亚砜体、高极性非对映体)
参考例1
N-[(4-氰基苯基)甲氧基甲基]丁基酰胺的制造
【化学式10】
将4-甲酰基苄腈(2.0g,15mmol)在氩气氛下溶解于氯仿(80mL),在室温下加入丁基酰胺(1.6g,18mmol)、甲醇钛(IV)(4.7g,27mmol),并在45℃下搅拌3小时。然后,在室温下搅拌16小时后,升温至45℃,搅拌6.5小时。向反应溶液中加入0.5M碳酸钾水溶液,并搅拌25分钟。加入醋酸乙酯,通过硅藻土过滤除去所析出的固体,并减压浓缩滤液。通过硅胶柱层析精制得到的残渣,从而得到标题化合物(2.9g,13mmol)。
收率:83%
参考例2
N-[(4-氰基苯基)甲氧基甲基]-N-甲基丁基酰胺的制造
【化学式11】
将N-[(4-氰基苯基)甲氧基甲基]丁基酰胺(2.8g,12mmol)溶解于四氢呋喃(40mL),冰冷下,加入碘甲烷(2.2g,16mmol)、氢化钠(0.62g,16mmol),并在室温下搅拌3.3小时。冷却至0℃,加入水停止反应,用叔丁基甲基醚提取。将有机层用饱和食盐水清洗后,用硫酸钠干燥,减压浓缩。通过硅胶柱层析精制得到的残渣,从而得到标题化合物(1.0g,4.2mmol)。
收率:35%
参考例3
N-{[4-(N’-羟基甲脒基)苯基]甲氧基甲基}-N-甲基丁基酰胺的制造
【化学式12】
将N-[(4-氰基苯基)甲氧基甲基]-N-甲基丁基酰胺(0.96g,3.9mmol)溶解于乙醇(15mL),加入三乙基胺(0.99g,9.8mmol)、羟基胺盐酸盐(0.68g,9.8mmol),加热回流下搅拌1.5小时。然后,减压下除去乙醇,加入水,并用醋酸乙酯提取。将有机层用饱和食盐水清洗后,用硫酸钠干燥,减压浓缩,从而得到标题化合物(1.1g,3.9mmol)。
收率:定量
参考例4
2-(甲基硫基)-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲醛的制造
【化学式13】
将2-氟-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲醛(1.0g,3.9mmol)溶解于二甲基乙酰胺(25mL),加入甲硫醇钠(0.32g,4.6mmol),并在45℃下搅拌1小时后,室温下静置17小时。然后,加入水,并用MTBE提取。将有机层用饱和食盐水清洗后,用硫酸钠干燥,减压浓缩。通过硅胶柱层析精制得到的残渣,从而得到标题化合物(0.87g,3.0mmol)。
收率:79%
物性值:熔点93-94℃
以下,示出制剂的实施例,但不限定于此。制剂例中,份表示重量份。
制剂例1.
将以上均匀混合并溶解,制得乳剂。
制剂例2.
本发明的通式(I)表示的化合物 3份
粘土粉末 82份
硅藻土粉末 15份
将以上均匀混合并溶解,制得粉剂。
制剂例3.
本发明的通式(I)表示的化合物 5份
膨润土与粘土的混合粉末 90份
木质素磺酸钙 5份
将以上均匀混合,加入适量的水并混练、造粒、干燥,制得粒剂。
制剂例4.
本发明的通式(I)表示的化合物 20份
高岭土与合成高分散硅酸 75份
聚氧乙烯壬基苯基醚与烷基苯磺酸钙的混合物 5份
将以上均匀混合并粉碎,制得可湿性粉剂。
试验例1.对于黄豆锈病的杀菌效果试验
将按照制剂例1至4所制备的以本发明的通式(I)表示的化合物为有效成分的药剂用水稀释至规定浓度,按照每1盆10ml的比例对在直径6cm的盆中育苗的黄豆(品种:Enrei,二叶期)上进行茎叶散布。药液风干后,从罹患黄豆锈病菌(Phakopsorapachyrhizi)的黄豆叶片上获得孢子,并由该孢子制备孢子悬浮液,喷雾接种该孢子悬浮液之后,在20℃的加湿条件下保持24小时,然后,转移至温室内放置10日左右。
评价时,确定各种发病面积比率,并由下述式1算出防治值。
【式1】
判定标准
0:防治值为9%以下;
1:防治值为10~19%;
2:防治值为20~29%;
3:防治值为30~39%;
4:防治值为40~49%;
5:防治值为50~59%;
6:防治值为60~69%;
7:防治值为70~79%;
8:防治值为80~89%;
9:防治值为90~99%;
10:防治值为100%。
上述试验结果表明,在本发明的通式(I)表示的化合物中,至少化合物编号1-7、1-13、1-14、1-15、1-19、1-22、1-25、1-28、1-37、1-39、1-40、1-42、1-43、1-44、1-45、1-46、1-47、1-48、1-49、1-52、1-53、1-54、1-55、1-56、1-57、1-58、1-62、1-68、1-69、1-71、1-78、1-82、1-95、1-104、1-105、1-106、1-107、1-108、1-109、1-110、1-111、1-112、1-113、1-114、1-115、1-129、1-130、1-140、1-141、1-142、1-143、1-144、1-145、1-146、1-147、1-148、1-149、1-150、1-151、1-152、1-154、1-155、1-156,1-157及1-158的化合物在50ppm的处理浓度下显示出判定标准8以上的效果(上述各化合物编号与表1中所示的化合物编号对应)。
工业可用性
本发明的通式(I)表示的化合物或其盐类作为农园艺用杀菌剂具有优异的效果。因此,本发明大大有利于农药工业、农业、及它们相关领域的发展。
Claims (6)
1.一种通式(I)表示的化合物或其盐类,
【化学式1】
式中,R1表示:
(a1)氢原子;
(a2)(C1-C6)烷基;
(a3)(C2-C6)烯基;
(a4)(C2-C6)炔基;
(a5)(C3-C6)环烷基;
(a6)卤代(C1-C6)烷基;
(a7)卤代(C2-C6)烯基;
(a8)卤代(C2-C6)炔基;或
(a9)卤代(C3-C6)环烷基,
R2表示:
(b1)氢原子;
(b2)(C1-C6)烷基;
(b3)(C2-C6)烯基;
(b4)(C2-C6)炔基;
(b5)(C3-C6)环烷基;
(b6)卤代(C1-C6)烷基;
(b7)卤代(C2-C6)烯基;
(b8)卤代(C2-C6)炔基;或
(b9)卤代(C3-C6)环烷基,
R3表示:
(c1)氢原子;
(c2)(C1-C6)烷基;
(c3)(C2-C6)烯基;
(c4)(C2-C6)炔基;
(c5)(C3-C6)环烷基;
(c6)(C1-C6)烷基羰基;或
(c7)(C1-C6)烷氧基羰基,
R4表示:
(d1)氢原子;
(d2)(C1-C6)烷基;
(d3)(C2-C6)烯基;
(d4)(C2-C6)炔基;
(d5)(C3-C6)环烷基;
(d6)(C1-C6)烷氧基;
(d7)卤代(C1-C6)烷基;
(d8)卤代(C2-C6)烯基;
(d9)卤代(C2-C6)炔基;
(d10)卤代(C3-C6)环烷基;
(d11)卤代(C1-C6)烷氧基;
(d12)Ra(Rb)N基,式中,Ra及Rb分别独立地表示氢原子、(C1-C6)烷基、(C3-C6)环烷基、(C3-C6)环烷基(C1-C6)烷基、苯基、(C1-C6)烷基羰基或苯基羰基;
(d13)芳基;
(d14)环上具有1~8个取代基的芳基,所述取代基分别独立地选自由卤素原子、氰基、硝基、(C1-C6)烷基、(C1-C6)烷氧基、(C3-C6)环烷基、卤代(C1-C6)烷基、卤代(C1-C6)烷氧基、卤代(C3-C6)环烷基、(C1-C6)烷基硫基、(C1-C6)烷基亚磺酰基、(C1-C6)烷基磺酰基、卤代(C1-C6)烷基硫基、卤代(C1-C6)烷基亚磺酰基及卤代(C1-C6)烷基磺酰基构成的组;
(d15)杂芳基;
(d16)环上具有1~3个取代基的杂芳基,所述取代基分别独立地选自由卤素原子、氰基、硝基、(C1-C6)烷基、(C1-C6)烷氧基、(C3-C6)环烷基、卤代(C1-C6)烷基、卤代(C1-C6)烷氧基、卤代(C3-C6)环烷基、(C1-C6)烷基硫基、(C1-C6)烷基亚磺酰基、(C1-C6)烷基磺酰基、卤代(C1-C6)烷基硫基、卤代(C1-C6)烷基亚磺酰基及卤代(C1-C6)烷基磺酰基构成的组;
(d17)芳基(C1-C6)烷基;
(d18)环上具有1~8个取代基的芳基(C1-C6)烷基,所述取代基分别独立地选自由卤素原子、氰基、硝基、(C1-C6)烷基、(C1-C6)烷氧基、(C3-C6)环烷基、卤代(C1-C6)烷基、卤代(C1-C6)烷氧基、卤代(C3-C6)环烷基、(C1-C6)烷基硫基、(C1-C6)烷基亚磺酰基、(C1-C6)烷基磺酰基、卤代(C1-C6)烷基硫基、卤代(C1-C6)烷基亚磺酰基及卤代(C1-C6)烷基磺酰基构成的组;
(d19)杂芳基(C1-C6)烷基;
(d20)环上具有1~3个取代基的杂芳基(C1-C6)烷基,所述取代基分别独立地选自由卤素原子、氰基、硝基、(C1-C6)烷基、(C1-C6)烷氧基、(C3-C6)环烷基、卤代(C1-C6)烷基、卤代(C1-C6)烷氧基、卤代(C3-C6)环烷基、(C1-C6)烷基硫基、(C1-C6)烷基亚磺酰基、(C1-C6)烷基磺酰基、卤代(C1-C6)烷基硫基、卤代(C1-C6)烷基亚磺酰基及卤代(C1-C6)烷基磺酰基构成的组;
(d21)链上具有1~3个取代基的(C1-C6)烷基,所述取代基分别独立地选自由氰基、(C1-C6)烷氧基、Ra(Rb)N基(式中,Ra及Rb如上所述)、(C1-C6)烷基硫基、(C1-C6)烷基亚磺酰基及(C1-C6)烷基磺酰基构成的组;或
(d22)环上具有1~2个氧原子的3元~6元非芳香族杂环基,
X1、X2、X3及X4分别独立地表示:
(e1)氢原子;
(e2)卤素原子;
(e3)氰基;
(e4)硝基;
(e5)(C1-C6)烷基;
(e6)(C3-C6)环烷基;
(e7)(C1-C6)烷氧基;
(e8)卤代(C1-C6)烷基;
(e9)卤代(C1-C6)烷氧基;
(e10)卤代(C3-C6)环烷基;
(e11)(C1-C6)烷基硫基;
(e12)(C1-C6)烷基亚磺酰基;
(e13)(C1-C6)烷基磺酰基;
(e14)卤代(C1-C6)烷基硫基;
(e15)卤代(C1-C6)烷基亚磺酰基;或
(e16)卤代(C1-C6)烷基磺酰基,
Y表示氧原子;或硫原子。
2.根据权利要求1所述的化合物或其盐类,其中,
R1为:
(a2)(C1-C6)烷基,
R2为:
(b1)氢原子,
R3为:
(c1)氢原子;
(c2)(C1-C6)烷基;或
(c5)(C3-C6)环烷基,
R4为:
(d2)(C1-C6)烷基;
(d3)(C2-C6)烯基;
(d4)(C2-C6)炔基;
(d5)(C3-C6)环烷基;
(d6)(C1-C6)烷氧基;
(d7)卤代(C1-C6)烷基;
(d12)Ra(Rb)N基,式中,Ra及Rb分别独立地表示氢原子、(C1-C6)烷基、(C3-C6)环烷基、(C3-C6)环烷基(C1-C6)烷基、苯基、(C1-C6)烷基羰基或苯基羰基;
(d13)芳基;
(d14)环上具有1~8个取代基的芳基,所述取代基分别独立地选自由卤素原子、氰基、硝基、(C1-C6)烷基、(C1-C6)烷氧基、(C3-C6)环烷基、卤代(C1-C6)烷基、卤代(C1-C6)烷氧基、卤代(C3-C6)环烷基、(C1-C6)烷基硫基、(C1-C6)烷基亚磺酰基、(C1-C6)烷基磺酰基、卤代(C1-C6)烷基硫基、卤代(C1-C6)烷基亚磺酰基及卤代(C1-C6)烷基磺酰基构成的组;
(d15)杂芳基;
(d17)芳基(C1-C6)烷基;
(d21)链上具有1~3个取代基的(C1-C6)烷基,所述取代基分别独立地选自由氰基、(C1-C6)烷氧基、Ra(Rb)N基(式中,Ra及Rb如上所述。)、(C1-C6)烷基硫基、(C1-C6)烷基亚磺酰基及(C1-C6)烷基磺酰基构成的组;或
(d22)环上具有1~2个氧原子的3元~6元非芳香族杂环基,
X1、X2、X3及X4分别独立地为:
(e1)氢原子;
(e2)卤素原子;
(e5)(C1-C6)烷基;
(e7)(C1-C6)烷氧基;
(e11)(C1-C6)烷基硫基;
(e12)(C1-C6)烷基亚磺酰基;或
(e13)(C1-C6)烷基磺酰基。
3.根据权利要求1或2所述的化合物或其盐类,其中,
R3为:
(c1)氢原子;或
(c2)(C1-C6)烷基,
X1、X2、X3及X4分别独立地为:
(e1)氢原子;
(e2)卤素原子;或
(e7)(C1-C6)烷氧基,
Y为氧原子。
4.一种农园艺用杀菌剂,其特征在于,含有权利要求1~3中任一项所述的化合物或其盐类作为有效成分。
5.一种植物病害的防治方法,其特征在于,利用有效量的权利要求4所述的农园艺用杀菌剂对植物或土壤进行处理。
6.权利要求1~3中任一项所述的化合物或其盐类作为农园艺用杀菌剂的应用。
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